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

HRID 2371097Notes

Reaction equation

HRID 2371097 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) and triphenylphosphine (7.11 g) were added to a stirred solution of biphenyl-4-yl-methanol (5.00 g) in dichloromethane (100 ml) at room temperature and stirred the reaction mixture for approximately 2 hours at the same temperature. The solvent was evaporated under reduced pressure and the residue thus obtained was purified by column chromatography using 5% diethylether in hexane as eluant to furnish the title compound (6.37 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue thus obtained
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7603e7040ae1435593aeb53237f98770
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

Loading…