Toluene → 3-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred solution of 4.27 g (16.6 mmol) of 2-(N-t-butylsulfamoyl)phenylboronic acid (from Step D), 32 mmol (26 mL of a 1.25N aqueous solution) of NaOH in 40 mL of ethanol was added 1.89 g (10 mmol, 1.27 mL) of 4-bromo-2-fluorotoluene, 60 mL of toluene, and 289 mg (0.25 mmol) of tetrakis(tfiphenylphosphine)palladium. The mixture was stirred at 90° C. for 4.5 h, cooled to room temperature, and the volatiles were removed in vacuo. The residue was extracted with ethyl acetate (3×) and the combined organic layers were washed with water, brine, and dried (Na2SO4). The crude product obtained after filtration and removal of solvents was flash chromatographed over silica gel (elution with hexane-EtOAc) to afford 2.96 g (92%) of the desired product cleanly (TLC in 4:1 hexane-EtOAc) as an off-white foam; mass spectrum (FAB) m/e 322 (M+1)+.

Provenance & Evidence