Carbon Dioxide → 2-Fluorobiphenyl-4-carboxylic Acid

Participants

Reaction Conditions

Reaction Steps

Few crystals of iodine are added to tetrahydrofuran (1400 mL) containing magnesium turnings (25.17 g, 1.035 mol). The mixture is heated at 60-70° C. A solution of 4-bromo-2-fluorobiphenyl (200 g, 0.797 mol) in tetrahydrofuran (600 mL) is added dropwise to the reaction mixture and refluxed for 1 hr. Reaction mixture is brought to room temperature and then cooled to −20° C. Carbon dioxide gas is passed through the reaction mixture for 45 minutes. The reaction mixture is treated with 3N HCl (500 mL) and extracted with ethyl acetate (2×500 mL). Combined organic layer is dried over sodium sulphate. Removal of solvent under reduced pressure gives a solid which is washed with diethyl ether (2×200 mL) and then dried to furnish 2-fluorobiphenyl-4-carboxylic acid.

Provenance & Evidence