Carbon tetrabromide → 3-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

HRID 1157738Notes

Reaction equation

HRID 1157738 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:16][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

Product 1

HCID 116013693-(Bromomethyl)-5-(trifluoromethyl)benzonitrileYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (10 ml) of 3-hydroxymethyl-5-trifluoromethylbenzonitrile (1.00 g) and carbon tetrabromide (1.81 g) in dichloromethane was added triphenylphosphine (1.37 g) with stirring under ice-cooling, and the mixture was continuously stirred for 30 min. The reaction solution was concentrated and the obtained residue was purified by column chromatography (n-hexane:ethyl acetate=9:1) to give the title compound (1.11 g, 84%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was continuously stirred for 30 min
  3. concentrationThe reaction solution was concentrated
  4. customthe obtained residue was purified by column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-d0e8ac7213c046a9adf90d4b7f830891
Source dataset
uspto-grants-2010_10
Patent number
US07807701B2

Reaction notes

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