3-Hydroxybenzyl alcohol → 3-(Bromomethyl)phenol

HRID 1475227Notes

Reaction equation

HRID 1475227 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:30]>C(Cl)Cl>[Br:30][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 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-hydroxybenzylalcohol (1.0 g, 8.06 mmol) and PPh3 (3.17 g, 12.08 mmol) in DCM (40 mL) at 0° C. was added CBr4 (4.01 g, 12.08 mmol) dropwise. The reaction was warmed to RT over 90 minutes, concentrated under reduced pressure and purified by silica gel chromatography (5% to 50% EtOAc in Hexanes) to give 3-(bromomethyl)phenol as a light brown crystalline solid (1.24 g, 82%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by silica gel chromatography (5% to 50% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-c1a5bbfbe1554db0928842fb3f04879e
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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