Water → Methyl 3-bromo-4-(difluoromethoxy)benzoate

Participants

Reaction Conditions

Reaction Steps

Ethyl chlorodifluoroacetate (1.12 ml, 8.7 mmol) was added to a mixture of methyl 3-bromo-4-hydroxybenzoate (Description 64, 2.0 g, 8.7 mmol) and potassium carbonate (1.2 g, 8.7 mmol) in N,N-dimethylformamide (20 ml) and the mixture was heated at 65° C. for 16 h. The mixture was cooled, water (100 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane/EtOAc (95:5) to give the title compound as a colorless solid (1.20 g, 49%). 1H NMR (250 MHz, CDCl3) δ8.31 (1 H, d, J 2.0 Hz), 8.22 (1 H, dd, J 8.5, 2.0 Hz), 7.05 (1 H, m), 6.61 (1 H, t, J 73 Hz), and 3.93 (3 H, s).

Provenance & Evidence