反応 #1904054

反応方程式

hydrogen chloride

triethyl amine

chloroacetyl chloride

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

→

title compound

収率 96.5%

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

収率 96.5%

溶媒

Ethyl acetate

diethyl ether

THF

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   その他organic layer separated
3. 3
   乾燥dried (Mg2SO4)
4. 4
   濃縮concentrated

実験手順

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).

出典