Carbon tetrabromide → 2-(Bromomethyl)benzyl alcohol

HRID 1586038Notes

Reaction equation

HRID 1586038 reaction equation
[C:1]1([CH2:9]O)[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[OH:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][Br:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 691531,2-Benzenedimethanol

Product 1

HCID 109435222-(Bromomethyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chomatographed (flash silica gel, 1:1 t-butyl methyl ether:hexanes) to afford the title compound as a white solid. (0.99 g, 49%)

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c96dce6767e740298143e8a82f91ca61
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

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