Ethyl bromoacetate → Ethyl 2-(4-bromo-2-nitrophenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-nitro-phenol (3.28 g, 15.0 mmol, 1 equiv) in dimethylformamide (40 mL) at 23° C. was added potassium carbonate (4.14 g, 30 mmol, 2 equiv) followed by ethyl bromoacetate (1.84 mL, 16.6 mmol, 1.1 equiv). The resulting mixture was warmed to 60° C. (oil bath) for 90 min then cooled to 23° C. The reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each). The organic layer was separated and washed successively with water, saturated brine solution (100 ml, each) then dried (MgSO4), filtered and concentrated to give 4.50 g (11.5 mmol, 77%) of the product as a yellow oil.

Provenance & Evidence