Carbon tetrabromide → 3-(Bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenyl

HRID 1391731Notes

Reaction equation

HRID 1391731 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[CH:10]=2)=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:20][CH2:15][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 144680034'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol

Product 1

HCID 468549613-(Bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenylYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [4′-(trifluoromethyl)-3-biphenylyl]methanol (177 mg, 0.70 mmol) in dry DCM (10 mL) was cooled to 0° C. (ice/water bath) under nitrogen and treated with CBr4 (256 mg, 0.77 mmol) in one portion. PPh3 (202 mg, 0.77 mmol) was then added portion-wise and the resulting mixture stirred for 1 hour at this temperature and was then allowed to warm to rt. The resulting mixture was then reduced and the residue purified directly by SPE (silica, 10 g cartridge) eluting with cyclohexane:DCM afforded the title compound as a colourless oil (220 mg).

Workup

  1. customthe residue purified directly by SPE (silica, 10 g cartridge)
  2. washeluting with cyclohexane

Sources & evidence

ORD record
ord-30d12e4476114d2791bddaa8a9218952
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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