Hydrogen Bromide → 2-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

HRID 2303434Notes

Reaction equation

HRID 2303434 reaction equation
Cl.C([C:4]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[OH:6])#N.Br.FC1C=CC(CC(O)=O)=CC=1>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:4][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[O:6])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 98372-(4-Fluorophenyl)acetic acidHCID 69661060HCID 69661060, compound

Product 1

HCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

Procedure

40.6 g (0.15 mol) of 2-cyano-2-(4-fluorophenyl)-1-(4-pyridyl)ethen-1-ol hydrochloride were refluxed with vigorous stirring for 19 h in 130 ml of 48% strength hydrobromic acid. The reaction mixture was cooled in an ice bath, and the precipitate deposited (4-fluorophenylacetic acid) was filtered off and washed with dist. water. On neutralizing the filtrate with 80 ml of ammonia water, the title compound deposited as a dark-green precipitate. The precipitate was filtered off, washed with dist. water and dried over P2O5 in vacuo: pale gray-beige powder. Yield: 14.2 g (45%).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationwas filtered off
  3. washwashed with dist
  4. filtrationThe precipitate was filtered off
  5. washwashed with dist
  6. dry with materialwater and dried over P2O5 in vacuo

Sources & evidence

ORD record
ord-1aaa501099f6428a84a792eb41f72918
Source dataset
uspto-grants-2002_08
Patent number
US06432988B1

Reaction notes

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