Reacción #1904054

Ecuación de reacción

hydrogen chloride

triethyl amine

chloroacetyl chloride

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

→

title compound

Rendimiento 96.5%

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

Rendimiento 96.5%

Disolventes

Ethyl acetate

diethyl ether

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter addition
2. 2
   Otroorganic layer separated
3. 3
   Secadodried (Mg2SO4)
4. 4
   Concentraciónconcentrated

Procedimiento

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).

Fuente