Hydrogen Bromide → 1-Phenyl-2-(4-pyridinyl)ethanone

Temperature

0 °C

A solution of diisopropylamine (22 mL, 15.03 mmol) in THF (200 mL) under argon atmosphere was cooled to −78° C. BuLi (96 mL of a 1.6 M solution in hexane, 153.0 mmol) was added dropwise. After 1 h, a solution of 4-methylpyridine (15.00 g, 161.1 mmol) in THF (75 mL) was added and allowed to warm to 0° C. At this temperature it was stirred for 30 minutes. It was cooled to −78° C. and benzonitrile (18.27 g, 177.2 mmol) in THF (75 mL) was added and stirred at −78° C. for 2 h. It was stirred at room temperature overnight. Water (225 mL) was added, it was cooled with a water-ice bath and adjusted to pH 1 with 48% HBr. The organic phase was separated. The aqueous phase was heated to reflux for 2 h, allowed to cool and extracted with diethyl ether. The aqueous phase was taken to neutral pH with 1 N NaOH and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness, to afford 28.53 g of title compound (yield: 90%).

1. temperatureIt was cooled to −78° C.
2. stirringstirred at −78° C. for 2 h
3. stirringIt was stirred at room temperature overnight
4. temperatureit was cooled with a water-ice bath
5. customThe organic phase was separated
6. temperatureThe aqueous phase was heated
7. temperatureto reflux for 2 h
8. temperatureto cool
9. extractionextracted with diethyl ether
10. extractionextracted with EtOAc
11. dry with materialThe organic phase was dried over Na2SO4
12. concentrationconcentrated to dryness

ORD record

ord-f973821d6aa6430d859b9375cd76b18f

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468376B2