863870-92-2 (4-溴-2-苯基苯并呋喃,Benzofuran,4-bromo-2-phenyl-)

快速询单

结构式：

4-溴-2-苯基苯并呋喃MOL文件

CAS号：

863870-92-2

中文名称：

4-溴-2-苯基苯并呋喃

英文名称：

Benzofuran,4-bromo-2-phenyl-

分子式：

C₁₄H₉BrO

分子量：

273.124663114548

4-溴-2-苯基苯并呋喃(863870-92-2)名称与标识符

名称

中文别名：

4-溴-2-苯基苯并呋喃;

英文别名：

Benzofuran,4-bromo-2-phenyl-;4-BROMO-2-PHENYLBENZOFURAN;4-Bromo-2-phenylbenzofuran (ACI);4-bromo-2-phenyl-1-benzofuran;AKOS027380973;D72205;CS-0097135;DTXSID60460989;CS-16414;863870-92-2;

标识符

InChIKey：

JFJOZPUPENSWRH-UHFFFAOYSA-N

Inchi：

1S/C14H9BrO/c15-12-7-4-8-13-11(12)9-14(16-13)10-5-2-1-3-6-10/h1-9H

SMILES：

BrC1C2=C(OC(C3C=CC=CC=3)=C2)C=CC=1

4-溴-2-苯基苯并呋喃(863870-92-2)物化性质

实验特性

折射率 : 1.652
沸点 : 375.6°C at 760 mmHg
闪点 : 181°C
密度 : 1.454

计算特性

精确分子量 : 271.98368g/mol
氢键供体数量 : 0
氢键受体数量 : 1
可旋转化学键数量 : 1
同位素质量 : 271.98368g/mol
重原子数量 : 16
复杂度 : 237
同位素原子数量 : 0
确定原子立构中心数量 : 0
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 4.7
拓扑分子极性表面积 : 13.1Å²

4-溴-2-苯基苯并呋喃(863870-92-2)推荐厂家更多厂家(7)

公司名称	手机号/电话	联系人	QQ	询单
上海瀚思化工有限公司	18939883912 021-34536277	顾经理	3003949364	询单
金锦乐（湖南）化学有限公司		金锦乐	1226360695	询单
江苏艾康生物医药研发有限公司	18795912720 025-66061636	杨情情	3004779232	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
上海源叶生物科技有限公司	15026964105 15026964105	汤思磊	2881489226	询单

4-溴-2-苯基苯并呋喃(863870-92-2)合成路线

合成路线：1 步

937716-64-8

863870-92-2

92104-02-4

反应条件：

1.1 Reagents: 4-(Dimethylamino)pyridine , Acetic acid, trifluoro-, anhydride with trifluoromethanesulfonic acid Solvents: Dichloromethane ; 3 h, rt

参考文献：

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans

Takeda, Norihiko; Miyata, Okiko; Naito, Takeaki, European Journal of Organic Chemistry, 2007, (9), 1491-1509

合成路线：1 步

2227105-14-6

100-52-7

_97%

863870-92-2

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ; 2 h, 50 °C

参考文献：

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

Zheng, Hong-Xing; et al, Organic Letters, 2018, 20(11), 3310-3313

合成路线：1 步

855836-52-1

536-74-3

_90%

863870-92-2

反应条件：

1.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：1 步

855836-52-1

536-74-3

_90%

863870-92-2

反应条件：

1.1 Reagents: Diethylamine , Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Twofold Unsymmetrical C-H Functionalization of PyrDipSi-Substituted Arenes: A General Method for the Synthesis of Substituted meta-Halophenols

Sarkar, Dhruba; et al, Angewandte Chemie, 2013, 52(41), 10800-10804

合成路线：1 步

855836-52-1

536-74-3

_72%

863870-92-2

反应条件：

1.1 Reagents: Piperidine , Cuprous iodide Catalysts: Bis(triphenylphosphine)palladium diacetate Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

A New and Efficient Synthesis of 4-Functionalized Benzo[b]furans from 2,3-Dihalophenols

Sanz, Roberto; et al, Journal of Organic Chemistry, 2005, 70(16), 6548-6551

合成路线：1 步

863870-79-5

536-74-3

_71%

863870-92-2

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 4 h, reflux; reflux → rt
1.2 Reagents: Piperidine Catalysts: Cuprous iodide , (SP-4-1)-Bis(acetato-κO)bis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

Aggregation-responsive ON-OFF-ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

Hamada, Hiroyoshi; et al, Materials Chemistry Frontiers, 2018, 2(2), 296-299

合成路线：1 步

863870-72-8

28995-88-2

_56%

863870-92-2

反应条件：

1.1 Reagents: sec-Butyllithium Solvents: Tetrahydrofuran , Cyclohexane ; 5 min, -78 °C → -65 °C; 90 min, -65 °C
1.2 -65 °C → rt; 30 min, rt
1.3 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide ; 8 h, 140 °C

参考文献：

Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions

Feberero, Claudia ; et al, Molecules, 2022, 27(2),

合成路线：2 步

108-95-2

93701-32-7

863870-92-2

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 10 min, rt
1.2 overnight, rt
1.3 Reagents: Water ; rt
2.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ; 2 h, 50 °C

参考文献：

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

Zheng, Hong-Xing; et al, Organic Letters, 2018, 20(11), 3310-3313

合成路线：2 步

1542203-43-9

863870-92-2

反应条件：

1.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：2 步

1542203-43-9

863870-92-2

反应条件：

1.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
1.2 Reagents: Ammonium chloride Solvents: Dichloromethane , Water ; rt
2.1 Reagents: Diethylamine , Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Twofold Unsymmetrical C-H Functionalization of PyrDipSi-Substituted Arenes: A General Method for the Synthesis of Substituted meta-Halophenols

Sarkar, Dhruba; et al, Angewandte Chemie, 2013, 52(41), 10800-10804

合成路线：2 步

863870-72-8

863870-92-2

反应条件：

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran , Hexane ; 30 min, -78 °C
1.2 Reagents: Iodine ; 30 min, -78 °C; -78 °C → rt
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 4 h, reflux; reflux → rt
2.2 Reagents: Piperidine Catalysts: Cuprous iodide , (SP-4-1)-Bis(acetato-κO)bis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

Aggregation-responsive ON-OFF-ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

Hamada, Hiroyoshi; et al, Materials Chemistry Frontiers, 2018, 2(2), 296-299

合成路线：3 步

863870-72-8

863870-92-2

反应条件：

1.1 Reagents: Diisopropylamine , Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C; 0 °C → -78 °C
1.2 30 min, -78 °C
1.3 Reagents: Iodine ; 30 min, -78 °C; -78 °C → rt
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 5 h, reflux
2.2 Reagents: Hydrochloric acid Solvents: Water ; neutralized, rt
3.1 Reagents: Piperidine , Cuprous iodide Catalysts: Bis(triphenylphosphine)palladium diacetate Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

A New and Efficient Synthesis of 4-Functionalized Benzo[b]furans from 2,3-Dihalophenols

Sanz, Roberto; et al, Journal of Organic Chemistry, 2005, 70(16), 6548-6551

合成路线：2 步

863870-79-5

863870-92-2

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 4 h, reflux
2.1 Reagents: Piperidine Catalysts: Cuprous iodide , (SP-4-1)-Bis(acetato-κO)bis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

Aggregation-responsive ON-OFF-ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

Hamada, Hiroyoshi; et al, Materials Chemistry Frontiers, 2018, 2(2), 296-299

合成路线：2 步

863870-79-5

863870-92-2

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 5 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ; neutralized, rt
2.1 Reagents: Piperidine , Cuprous iodide Catalysts: Bis(triphenylphosphine)palladium diacetate Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

A New and Efficient Synthesis of 4-Functionalized Benzo[b]furans from 2,3-Dihalophenols

Sanz, Roberto; et al, Journal of Organic Chemistry, 2005, 70(16), 6548-6551

合成路线：3 步

1013031-65-6

863870-92-2

反应条件：

1.1 Reagents: Hydrogen bromide Solvents: Acetic acid , Water ; rt; 2 h, 100 °C; 100 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ; pH 10, rt
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 10 min, rt
2.2 overnight, rt
2.3 Reagents: Water ; rt
3.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ; 2 h, 50 °C

参考文献：

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

Zheng, Hong-Xing; et al, Organic Letters, 2018, 20(11), 3310-3313

合成路线：3 步

1542203-03-1

863870-92-2

反应条件：

1.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
1.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
2.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water ; rt
3.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：3 步

1542203-03-1

863870-92-2

反应条件：

1.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
1.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
2.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
2.2 Reagents: Ammonium chloride Solvents: Dichloromethane , Water ; rt
3.1 Reagents: Diethylamine , Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Twofold Unsymmetrical C-H Functionalization of PyrDipSi-Substituted Arenes: A General Method for the Synthesis of Substituted meta-Halophenols

Sarkar, Dhruba; et al, Angewandte Chemie, 2013, 52(41), 10800-10804

合成路线：3 步

591-20-8

88-10-8

863870-92-2

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; rt; 2.5 h, rt
1.2 8 h, rt
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran , Hexane ; 30 min, -78 °C
2.2 Reagents: Iodine ; 30 min, -78 °C; -78 °C → rt
3.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 4 h, reflux; reflux → rt
3.2 Reagents: Piperidine Catalysts: Cuprous iodide , (SP-4-1)-Bis(acetato-κO)bis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

Aggregation-responsive ON-OFF-ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

Hamada, Hiroyoshi; et al, Materials Chemistry Frontiers, 2018, 2(2), 296-299

合成路线：4 步

591-20-8

88-10-8

863870-92-2

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; rt; 2 h, rt
1.2 Solvents: Tetrahydrofuran ; 8 h, rt
2.1 Reagents: Diisopropylamine , Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C; 0 °C → -78 °C
2.2 30 min, -78 °C
2.3 Reagents: Iodine ; 30 min, -78 °C; -78 °C → rt
3.1 Reagents: Sodium hydroxide Solvents: Ethanol ; 5 h, reflux
3.2 Reagents: Hydrochloric acid Solvents: Water ; neutralized, rt
4.1 Reagents: Piperidine , Cuprous iodide Catalysts: Bis(triphenylphosphine)palladium diacetate Solvents: Dimethylformamide ; 5 h, 60 °C

参考文献：

A New and Efficient Synthesis of 4-Functionalized Benzo[b]furans from 2,3-Dihalophenols

Sanz, Roberto; et al, Journal of Organic Chemistry, 2005, 70(16), 6548-6551

合成路线：4 步

1369625-72-8

3240-34-4

863870-92-2

反应条件：

1.1 Catalysts: Lithium acetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
1.2 Reagents: Triethylamine ; rt
2.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
2.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
3.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
3.2 Reagents: Ammonium chloride Solvents: Water ; rt
4.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：4 步

1369625-72-8

3240-34-4

863870-92-2

反应条件：

1.1 Reagents: Lithium acetate Catalysts: Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
1.2 Reagents: Triethylamine ; rt
2.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
2.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
3.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
3.2 Reagents: Ammonium chloride Solvents: Dichloromethane , Water ; rt
4.1 Reagents: Diethylamine , Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Twofold Unsymmetrical C-H Functionalization of PyrDipSi-Substituted Arenes: A General Method for the Synthesis of Substituted meta-Halophenols

Sarkar, Dhruba; et al, Angewandte Chemie, 2013, 52(41), 10800-10804

合成路线：4 步

601-84-3

863870-92-2

反应条件：

1.1 Reagents: Iodine , Sodium borohydride Solvents: Tetrahydrofuran ; 30 min, 0 °C; 12 h, 0 °C → reflux; reflux → rt
1.2 Solvents: Methanol ; 30 min, rt
1.3 Reagents: Potassium hydroxide Solvents: Water ; 4 h, rt
2.1 Reagents: Hydrogen bromide Solvents: Acetic acid , Water ; rt; 2 h, 100 °C; 100 °C → rt
2.2 Reagents: Sodium hydroxide Solvents: Water ; pH 10, rt
3.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 10 min, rt
3.2 overnight, rt
3.3 Reagents: Water ; rt
4.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ; 2 h, 50 °C

参考文献：

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

Zheng, Hong-Xing; et al, Organic Letters, 2018, 20(11), 3310-3313

合成路线：5 步

1369625-51-3

863870-92-2

反应条件：

1.1 Reagents: N-Bromosuccinimide Catalysts: Iodobenzene diacetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 26 h, 50 °C
2.1 Catalysts: Lithium acetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
2.2 Reagents: Triethylamine ; rt
3.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
3.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
4.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
4.2 Reagents: Ammonium chloride Solvents: Water ; rt
5.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：5 步

1369625-51-3

863870-92-2

反应条件：

1.1 Reagents: N-Bromosuccinimide , Iodobenzene diacetate Catalysts: Palladium diacetate Solvents: 1,2-Dichloroethane ; 26 h, 50 °C
2.1 Reagents: Lithium acetate Catalysts: Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
2.2 Reagents: Triethylamine ; rt
3.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
3.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
4.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
4.2 Reagents: Ammonium chloride Solvents: Dichloromethane , Water ; rt
5.1 Reagents: Diethylamine , Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Twofold Unsymmetrical C-H Functionalization of PyrDipSi-Substituted Arenes: A General Method for the Synthesis of Substituted meta-Halophenols

Sarkar, Dhruba; et al, Angewandte Chemie, 2013, 52(41), 10800-10804

合成路线：6 步

1369625-74-0

591-50-4

863870-92-2

反应条件：

1.1 Reagents: Tripotassium phosphate Catalysts: Dirhodium tetraacetate Solvents: 1,4-Dioxane ; 7 h, 90 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Iodobenzene diacetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 26 h, 50 °C
3.1 Catalysts: Lithium acetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
3.2 Reagents: Triethylamine ; rt
4.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
4.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
5.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
5.2 Reagents: Ammonium chloride Solvents: Water ; rt
6.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：7 步

31462-54-1

2227-29-4

863870-92-2

反应条件：

1.1 Reagents: Magnesate(1-), dichloro(1-methylethyl)-, lithium (1:1) Solvents: Tetrahydrofuran ; 0 - 5 °C; 1 h, 0 °C
1.2 Solvents: Tetrahydrofuran ; 0 °C → rt; overnight, rt
1.3 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Tripotassium phosphate Catalysts: Dirhodium tetraacetate Solvents: 1,4-Dioxane ; 7 h, 90 °C
3.1 Reagents: N-Bromosuccinimide Catalysts: Iodobenzene diacetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 26 h, 50 °C
4.1 Catalysts: Lithium acetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
4.2 Reagents: Triethylamine ; rt
5.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
5.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
6.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
6.2 Reagents: Ammonium chloride Solvents: Water ; rt
7.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：8 步

1722-12-9

863870-92-2

反应条件：

1.1 Reagents: Hydrogen iodide ; rt
2.1 Reagents: Magnesate(1-), dichloro(1-methylethyl)-, lithium (1:1) Solvents: Tetrahydrofuran ; 0 - 5 °C; 1 h, 0 °C
2.2 Solvents: Tetrahydrofuran ; 0 °C → rt; overnight, rt
2.3 Reagents: Ammonium chloride Solvents: Water ; rt
3.1 Reagents: Tripotassium phosphate Catalysts: Dirhodium tetraacetate Solvents: 1,4-Dioxane ; 7 h, 90 °C
4.1 Reagents: N-Bromosuccinimide Catalysts: Iodobenzene diacetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 26 h, 50 °C
5.1 Catalysts: Lithium acetate , Palladium diacetate Solvents: 1,2-Dichloroethane ; 28 h, 80 °C; 80 °C → rt
5.2 Reagents: Triethylamine ; rt
6.1 Reagents: Hydrofluoric acid Solvents: Tetrahydrofuran , Water ; 0 °C; 1 h, rt
6.2 Reagents: N-Iodosuccinimide , Silver fluoride Solvents: Tetrahydrofuran ; overnight, rt; 8 h, 70 °C
7.1 Reagents: Cesium carbonate Solvents: Methanol ; 0 °C; 3 h, rt
7.2 Reagents: Ammonium chloride Solvents: Water ; rt
8.1 Reagents: Piperidine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ; 10 h, 60 °C

参考文献：

Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C-H Functionalizations

Sarkar, Dhruba; et al, ACS Catalysis, 2015, 5(11), 6792-6801

合成路线：2 步

反应条件：

1.1 Catalysts: Hydrochloric acid Solvents: Ethanol , Water ; rt
2.1 Reagents: 4-(Dimethylamino)pyridine , Acetic acid, trifluoro-, anhydride with trifluoromethanesulfonic acid Solvents: Dichloromethane ; 3 h, rt

参考文献：

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans

Takeda, Norihiko; et al, European Journal of Organic Chemistry, 2007, (9), 1491-1509

合成路线：3 步

937716-83-1

863870-92-2

92104-02-4

反应条件：

1.1 Reagents: Hydrazine Solvents: Methanol , Chloroform ; 24 h, rt
2.1 Catalysts: Hydrochloric acid Solvents: Ethanol , Water ; rt
3.1 Reagents: 4-(Dimethylamino)pyridine , Acetic acid, trifluoro-, anhydride with trifluoromethanesulfonic acid Solvents: Dichloromethane ; 3 h, rt

参考文献：

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans

Takeda, Norihiko; et al, European Journal of Organic Chemistry, 2007, (9), 1491-1509