Dimethylformamide → tert-Butyl 4-bromo-2-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-2-fluorobenzoic acid (3.0 g, 0.014 mol) in THF (50 mL) at 0° C. was added DMF (0.1 mL) and oxalyl chloride (1.5 mL, 0.018 mol). The mixture was stirred at 0° C. for 1 h and then warmed to rt. The solvent was removed under reduced pressure. The obtained acid chloride was added to a mixture of tert-butyl alcohol (5.0 g, 0.067 mol), pyridine (10 mL), and CH2Cl2 (50 mL) at 0° C. The mixture was stirred at rt for 3 h, and then at 50° C. overnight. The mixture was washed with water, 2 N NaOH, and brine, dried (MgSO4), and concentrated under vacuum. The residue was purified by column to give a colorless oil (1.5 g, 45%).

Provenance & Evidence