Ammonium Chloride → 2-Bromo-5-(2-methylprop-1-en-1-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of (1-methylethyl)(triphenyl)phosphonium iodide (72.2 g) in N,N-dimethylformamide (200 mL) was added a solution of potassium tert-butoxide (20.1 g) in N,N-dimethylformamide (100 mL) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the reaction solution was added dropwise at 0° C. a solution of 6-bromopyridine-3-carbaldehyde (20.8 g) in N,N-dimethylformamide (200 mL). The reaction solution was warmed to room temperature, and the mixture was stirred at room temperature for 16 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-40:60, volume ratio) to give the title compound (16.2, yield 68%) as a colorless oil.

Provenance & Evidence