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

Temperature

0 °C

To a solution of (1-methylethyl)(triphenyl)phosphonium iodide (72.2 g) in N,N-dimethylformamide (200 mL) was added a solution of tert-butoxy potassium (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 a solution of 6-bromopyridine-3-carbaldehyde (20.8 g) in N,N-dimethylformamide (200 mL) at 0° C. The reaction solution was allowed to warm to room temperature, and stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, 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.

1. temperaturecooling
2. temperatureto warm to room temperature
3. stirringstirred at room temperature for 16 hr
4. extractionthe mixture was extracted with diethyl ether
5. washThe extract was washed successively with water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-40:60, volume ratio)

ORD record

ord-0261a1d575654c499e690aedb7f25190

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349886B2