溴苯 → 1-Phenyl-2-(thiophen-3-yl)ethanone

HRID 924924笔记

反应方程式

HRID 924924 反应方程式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.CON(C)[C:16](=[O:23])[CH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[C:2]1([C:16](=[O:23])[CH2:17][C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

6

反应物 4

HCID 7961溴苯HCID 25517氯化铵HCID 11423995N-methoxy-N-methyl-2-(thiophen-3-yl)acetamideHCID 178418339正丁基锂

产物 1

HCID 122331131-Phenyl-2-(thiophen-3-yl)ethanone收率 55%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
-78 °C

实验过程

To the solution of bromo-benzene (1.0 g, 6.36 mmol) in anhydrous THF (30 mL) was added n-BuLi (5.9 mmol, 2.4 mL) at −78° C. under nitrogen, and the mixture was stirred at −78° C. for further 20 min., a solution of N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide (1 g, 5.4 mmol) in anhydrous THF (10 mL) was added. The resulting mixture was stirred at −78° C. under nitrogen for about 30 min., poured into NH4Cl aqueous solution, and extracted with EtOAc. The organic layers were washed with brine, dried over sodium sulfate, concentrated, and purified by column chromatograph (PE:EtOAc=20:1) to afford Intermediate 2 as a colorless oil (600 mg, yield 55.0%).

后处理

  1. stirringThe resulting mixture was stirred at −78° C. under nitrogen for about 30 min.
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatograph (PE:EtOAc=20:1)

来源与证据

ORD记录
ord-3267aa9ccfab4d218c0f17036445456e
来源数据集
uspto-grants-2016_03
专利号
US09283229B2

反应笔记

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