Hydrogen Bromide → 1-(2-Bromopyridin-4-yl)-2-(4-fluorophenyl)ethanone

HRID 1017663

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8](=[O:19])[CH:9](C#N)[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[BrH:20]>C(=O)(O)[O-].[Na+]>[Br:20][C:2]1[CH:7]=[C:6]([C:8](=[O:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To 1-(2-chloropyridin-4-yl)-2-cyano-2-(4-fluorophenyl)ethanone (22.0 g, 80 mmol) was added 48% hydrobromic acid (75 ml) and the reaction mixture was heated at reflux in an oil bath at 135° C. After 4 h, the reaction mixture was allowed to cool to room temperature and then further cooled in an ice bath. Saturated sodium bicarbonate (100 ml) was carefully added, followed by solid portions of sodium bicarbonate until the pH of the reaction mixture was neutral. The reaction mixture was then extracted with ethyl acetate and the ethyl acetate layer was dried over sodium sulfate, filtered and concentrated to a brown semi-solid (2.8 g). The crude product was purified by flash chromatography on silica gel, eluting with 1:1 mixture of ethyl acetate/hexanes to give 1-(2-bromopyridin-4-yl)-2-(4-fluorophenyl)ethanone (1.9 g).

Workup

temperaturethe reaction mixture was heated
temperatureto cool to room temperature
temperaturefurther cooled in an ice bath
extractionThe reaction mixture was then extracted with ethyl acetate
dry with materialthe ethyl acetate layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated to a brown semi-solid (2.8 g)
customThe crude product was purified by flash chromatography on silica gel
washeluting with 1:1 mixture of ethyl acetate/hexanes

Sources & evidence

ORD record: ord-79eacb8b118a4364bfdc16d53c65f9d5
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479507B2

Linked notes

Loading…