反应 #217608

ord-d3c71c1d092349daaadbfda47e4a40e0

反应方程式

Cc1cc(Br)cs1
4-bromo-2-methylthiophene
CCN(CC)CC
N,N-diethylethanamine
CC1(C)OBOC1(C)C
4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Cc1cc(B2OC(C)(C)C(C)(C)O2)cs1
title compound ( D38 )
Cc1cc(B2OC(C)(C)C(C)(C)O2)cs1
4,4,5,5-Tetramethyl-2-(5-methyl-3-thienyl)-1,3,2-dioxaborolane

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度The reaction was cooled
  2. 2
    过滤filtered
  3. 3
    洗涤washing with tert-butyl methyl ether
  4. 4
    其他the residue purified by chromatography on silica gel (gradient of hexane to 3% ethyl acetate:hexane)

实验过程

To 4-bromo-2-methylthiophene (1.5 g, 8.5 mmol) in THF (17 ml) was added bis[(1,1-dimethylethyl)phosphanyl]palladium (218 mg, 0.43 mmol), then N,N-diethylethanamine (2.5 g, 25.4 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.63 g, 12.7 mmol) and the resulting mixture heated at 40° C. under argon for 2 hours. The reaction was cooled and then filtered, washing with tert-butyl methyl ether. The washings were reduced in vacuo and the residue purified by chromatography on silica gel (gradient of hexane to 3% ethyl acetate:hexane) to afford the title compound (D38). MS (ES+) m/e 225 [M+H]+.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07381728B2uspto-grants-2008_06