Dimethylformamide → Methyl 2'-fluoro-5'-(methyloxy)-2-nitro-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-chloro-3-nitrobenzoate (10.00 g, 46 mmol, commercially available from TCI) in DMF (15.00 mL, 194 mmol) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (12 g, 70 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), potassium carbonate (19 g, 139 mmol), and then tetrakis(triphenylphosphine)palladium (2.1 g, 1.9 mmol). The mixture was heated at 90° C. for 18 hours and then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. The organic layers were combined, dried over anhydrous MgSO4, and filtered. The organic solvent was removed under reduced pressure and the residue was purified on silica gel (0-40% EtOAc in hexanes) to yield T12.3 as a colorless oil (14.00 g, 99% yield).

Provenance & Evidence