Bromide ion → HCID 21767387, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyltriphenylphosphnium bromide (18.86 g, 52.8 mmol) in THF (120 mL) was added 0.5M potassium hexamethyldisilazide in toluene (106 mL, 53.0 mmol) at -10° C. The mixture was stirred for 40 min at the same temperature and 3-methyl-6-nitrobenzaldehyde (8.0 g, 48 mmol) in THF (60 mL) was added. The mixture was stirred for 1 h at -10° C. and 0.2N hydrochloric acid (400 mL) was added. The mixture was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 15:1 hexane/ethyl acetate to give 5.10 g of the title compound (65%).

Provenance & Evidence