2,3,4,6-tetrafluorobenzoic Acid → Tert-butyl 2,3,4,6-tetrafluorobenzoate

Participants

Reaction Conditions

Reaction Steps

Di-tert-butyl carbonate (3.63 g, 16.7 mmol) was added to a mixture of 2,3,4,6-tetrafluorobenzoic acid (1.60 g, 8.88 mmol), 4-dimethylaminopyridine (102 mg, 0.83 mmol) in tBuOH (20 mL) and heated at 40° C. for 16 hours. The reaction mixture was quenched with aqueous 1M HCl and extracted with EtOAc. Combined organics were washed with aqueous 1M NaOH, then brine and evaporated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 50% EtOAc in heptane to afford the title compound as a colourless oil (1.25 g, 59% yield):

Provenance & Evidence