Dichloromethane → Methyl 5-bromo-2-(2-(4-chlorophenoxy)acetamido)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-amino-5-bromobenzoate (3.03 mL, 17.4 mmol) in THF (28 mL) was added 2-(4-chlorophenoxy)acetyl chloride (3.92 g, 19.1 mmol) to form a suspension. An additional 30 mL of dichloromethane was added. The reaction was then cooled to 0° C. and triethylamine (5.32 mL, 38.3 mmol) was added dropwise. The cold bath was removed and the reaction was stirred at room temperature for 2 hours. Analysis showed the reaction to be incomplete, so additional 2-(4-chlorophenoxy)acetyl chloride (0.5 mL, 3.22 mmol) was added and reaction solution was stirred for 1 hour then transferred to a reparatory funnel with dichloromethane dilution. The organic phase was washed with water and saturated aqueous NH4Cl solution, then dried (MgSO4), filtered, and concentrated to yield the title compound.

Provenance & Evidence