Ethanol → Benzoic acid, 2,6-difluoro-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

2,6-Difluorobenzoyl chloride was diluted with CH2Cl2 (5 ml) and cooled to 0° C. A mixture of EtOH (1.2 ml, 20 mmol) and pyridine (1.6 ml, 20 mmol) was added, dropwise, over 5 minutes to the reaction mixture. The ice bath was removed after 5 minutes and the reaction mixture stirred at 25° C. for 45 min. The solvent and volatiles were evaporated under reduced pressure and the residue was partitioned between 1N HCl and EtOAc (10 ml each). The aqueous phase was separated and extracted with 2×7 ml EtOAc. The combined organic extracts was washed with NaHCO3 (10 ml), brine (7 ml), dried over MgSO4 and concentrated to give 1.562 g ethyl 2,6-difluorobenzoate as an almost colorless oil. (84% yield from steps B and C).

Provenance & Evidence