反应 #1904054

反应方程式

hydrogen chloride

triethyl amine

chloroacetyl chloride

1-(2-amino-5-bromo-phenyl)-1-thiophen-2-yl-ethanol

→

title compound

收率 96.5%

N-[4-Bromo-2-(1-hydroxy-1-thien-2-ylethyl)phenyl]-2-chloroacetamide

收率 96.5%

溶剂

Ethyl acetate

diethyl ether

THF

反应条件

后处理

1. 1
   workup.ADDITIONAfter addition
2. 2
   其他organic layer separated
3. 3
   干燥dried (Mg2SO4)
4. 4
   浓缩concentrated

实验过程

To a solution of 1-(2-amino-5-bromo-phenyl)-1-thiophen-2-yl-ethanol (3.9 g, 13 mmol) in a mixture of anhydrous THF and diethyl ether (20 mL/20 mL) at 0° C. under nitrogen was added triethyl amine (4 mL, 28.7 mmol) and chloroacetyl chloride (1.6 mL, 20 mmol). After addition, the reaction mixture was slowly warmed to room temperature (rt), stirred for 3 h, and treated with a cold 1N hydrogen chloride aqueous solution (70 mL). Ethyl acetate (100 mL) was added and organic layer separated, dried (Mg2SO4), concentrated to yield the title compound as a white solid (4.7 g, 94%). 1H-NMR (DMSO-d6) δ 10.78 (s, 1H), 8.05 (d, J=8.7 Hz, 1H), 7.51 (dd, J=8.7, 2.2 Hz, 1H), 7.43 (d, J=5.0 Hz, 1H), 7.37 (m, 2H), 6.95 (m, 1H), 6.88 (dd, J=3.4, 0.8 Hz, 1H), 4.26 (d, J=6.9 Hz, 2H), 1.94 (s, 3H).

来源