Carbon tetrabromide → 1,1'-Biphenyl, 4-(bromomethyl)-

HRID 2382911Notes

Reaction equation

HRID 2382911 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=[CH:29][C:28](CO)=[CH:27][CH:26]=1>ClCCl>[Br:5][CH2:1][C:36]1[CH:37]=[CH:38][C:33]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19186(1,1'-Biphenyl)-4-methanol

Product 1

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-Yield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenyl phosphine (7.11 g, 27.1 mmol) were added to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 mmol) in dichloromethane (100 mL) at room temperature. Stirring was continued at room temperature for 1.5 hours then the solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane) to give the title compound (6.37 g, 95%) as a white solid. 1H NMR (400 MHz: CDCl3): 7.6 (4H), 7.45 (4H), 7.35 (1H), 4.55 (2H).

Workup

  1. customthe solvent removed by evaporation under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-703a9a60e3244558835c614424716067
Source dataset
uspto-grants-2012_09
Patent number
US08263602B2

Reaction notes

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