Dimethylformamide → Dimethyl 2'-fluoro-1,1'-biphenyl-2,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dimethyl 4-(trifluoromethylsulfonyloxy)isophthalate T9.2 (1.60 g, 4.7 mmol) in DMF (9.4 mL, 4.7 mmol) at 23° C. was added 2-fluorophenylboronic acid (0.98 g, 7.0 mmol, commercially available from Aldrich), potassium carbonate (1.9 g, 14 mmol), and then tetrakis(triphenylphosphine)palladium (0.54 g, 0.47 mmol). The reaction mixture was heated to 90° C. and the reaction was stirred for 22 hours. The reaction was then cooled to room temperature, diluted with water, and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield T19.1 as a colorless oil (1.10 g, 82% yield).

Provenance & Evidence