3-Hydroxybenzyl alcohol → 3-(Bromomethyl)phenol

HRID 641864Notes

Reaction equation

HRID 641864 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.[Br:10]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:10][CH2:5][C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 137401503-(Bromomethyl)phenolYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxybenzyl alcohol (4 g, 32.2 mmoles) in methylene chloride (250 ml), cooled at 0° C., tetrabromomethane (12.82 g, 38.6 mmoles) and triphenylphosphine (12.67 g, 48.3 mmoles) are added. The mixture is kept under stirring at 0° C. for 10 minutes, then evaporated at reduced pressure. The crude product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 8/2. 3.5 g of the expected compound are obtained.

Workup

  1. customevaporated at reduced pressure
  2. customThe crude product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 8/2

Sources & evidence

ORD record
ord-d6f04254c4eb470195f5db65a4aecb70
Source dataset
uspto-grants-2010_04
Patent number
US07696230B2

Reaction notes

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