Dimethyl Sulfoxide → 2-Acetyl-6-bromopyridine

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (2.1 mL, 3.81 mmol) in dry CH2Cl2 was cooled to −70° C. followed by adding DMSO (0.6 mL, 8.39 mmol) dropwise. After stirred for 5 min under −60° C., 1-(6-bromo-pyridin-2-yl)-ethanol (770 mg, 3.81 mmol) in dry CH2CL2 (10 mL) was added dropwise. After stirred for 30 min, TEA (2.7 mL, 19.83 mmol) was added and the resulting mixture was warmed to RT and stirred for 1 h. The reaction mixture was quenched with H2O. The organic layer was washed with H2O, brine, and dried over MgSO4. Solvent was removed and the crude compound was purified by chromatography on silica gel. Elution with hexane:acetone mixture (90:10) gave a white solid. MS m/z: 200.3(M+H). Calc'd. for C7H8BrNO-198.96.

Provenance & Evidence