Methanol → Methyl 3-fluoro-5-(3-fluorophenyl)-2-methyl-benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-3-fluoro-5-(3-fluorophenyl)-2-methyl-benzene (1.88 g, 6.6 mmol, 1 eq), potassium acetate (3.25 g, 33.2 mmol, 5 eq), palladium (II) acetate (0.12 g, 0.5 mmol, 0.075 eq) and dppf (0.41 g, 0.9 mmol, 0.15 eq) in a mixture of MeOH (50 mL) and THF (50 mL) was placed in a high pressure reactor and pressurized with carbon monoxide gas to 50 bar. The reaction mixture was heated at 125° C. for 16 h, then cooled, filtered and the solvent evaporated in vacuo. The residue was partitioned between water and CH2Cl2 and extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc 1:0 to 50:1) to give the title compound as a white solid (1 g, 57%).

Provenance & Evidence