Sodium Carbonate → 5'-Bromo-4-(ethylsulfonyl)-2,2'-difluorobiphenyl

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[4-(ethylsulfonyl)-2-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 45, 102 mg, 0.33 mmol) and 4-bromo-1-fluoro-2-iodobenzene (108 mg, 0.36 mmol) in toluene (0.56 mL) and ethanol (0.14 mL) was added aqueous Na2CO3 solution (1M, 0.55 mL, 0.55 mmol). A stream of nitrogen gas was bubbled through the reaction mixture for 5 minutes. Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (13 mg, 0.016 mmol) was then added, and the mixture was heated at 80° C. for 1 hour. The reaction mixture was cooled, diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 100:0 to 70:30 to afford the title compound as a light yellow solid in 57% yield, 67 mg.

Provenance & Evidence