Reaction #1904054

Reaction equation

hydrogen chloride

triethyl amine

chloroacetyl chloride

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

→

title compound

Yield 96.5%

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

Yield 96.5%

Solvents

Ethyl acetate

diethyl ether

THF

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition
2. 2
   Otherorganic layer separated
3. 3
   Dryingdried (Mg2SO4)
4. 4
   Concentrationconcentrated

Procedure

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).

Source