2-Bromoethanol → 2-Methyl-2-(4-nitrophenyl)-propionic acid, 2-bromo-ethyl ester

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (3 mL, 41 mmol) was added to 2-methyl-2-(4-nitrophenyl)-propionic acid (1 g, 4.78 mmol) and heated at 90° C. overnight. Excess thionyl chloride was evaporated to give a crude acid chloride which was dissolved in acetonitrile (8 mL). To this was added 2-bromoethanol (0.41 mL, 5.78 mmol) then the mixture was heated at reflux overnight. After concentration in vacuo, the residue was diluted with ethyl acetate and washed with sodium bicarbonate solution, then the organic layer was dried and evaporated to afford 2-methyl-2-(4-nitrophenyl)-propionic acid, 2-bromo-ethyl ester (0.99 g, 65.5%).

Provenance & Evidence