Dimethyl Sulfide → HCID 18380364, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-biphenyl-4-yl-1H-pyrrole (500 mg, 2.28 mmol), dimethylsulfide (0.25 mL, 3.4 mmol), CH2Cl2 (30 mL), and acetonitrile (10 mL) at −10° C. was added dropwise a solution of bromine in CH2Cl2 (5 mL) over 15 minutes. The mixture was allowed to warm to 10° C. over 2 hours. The resultant mixture was washed with 1M pH 7 phosphate buffer (50 mL) and extracted with CH2Cl2 (25 mL). The combined organic layers were dried over Na2SO4 and concentrated to a crude residue which was purified via flash column chromatography with 0-10% CH2Cl2/hex gradient eluant to furnish 240 mg (40%) of N-(biphenyl-4-yl)-3-bromo-1H-pyrrole as a white solid, mp 141-3° C.

Provenance & Evidence