Hydrogen Bromide → 2-Hydroxy-4-(trifluoromethyl)benzonitrile

HRID 1156538Notes

Reaction equation

HRID 1156538 reaction equation
C([O:8][C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1.Br>C(O)(=O)C>[OH:8][C:9]1[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 20534827HCID 20534827, compound

Product 1

HCID 205348362-Hydroxy-4-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(Benzyloxy)-4-(trifluoromethyl)benzonitrile (~20 grams) in 350 ml. acetic acid and 100 ml. 33% HBr was stirred overnight, refluxed for four hours, and then stirred overnight again. Next the reaction mixture was stripped to a small volume and poured into ice water. The crude precipitate which formed was stirred in hexane, filtered, and was identified by NMR as the desired product, yield 9.3 grams.

Workup

  1. temperaturerefluxed for four hours

Sources & evidence

ORD record
ord-53f55004358b47a6b23b116404cae3a8
Source dataset
uspto-grants-1982_06
Patent number
US04336264

Reaction notes

Loading…