3-Hydroxybenzyl alcohol → 3-(Bromomethyl)phenol

HRID 910745Notes

Reaction equation

HRID 910745 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[OH:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:5][CH2:1][C:13]1[CH:14]=[C:7]([OH:6])[CH:8]=[CH:9][CH:12]=1

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 137401503-(Bromomethyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C. and under a nitrogen atmosphere carbontetrabromide (28.05 g) was added over a period of 20 min to a suspension of 3-hydroxybenzylalcohol (7 g) and triphenylphosphine (22.18 g) in dichloromethane (250 ml). After stirring for 1 h at 0° C., the reaction mixture was concentrated in vacuo. The residue was chromatographed on silica gel in heptane/ethyl acetate=2/1 (v/v) as eluent. Yield: 10 g. MS-ESI: [M−H]-=184.8/186.8

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was chromatographed on silica gel in heptane/ethyl acetate=2/1 (v/v) as eluent

Sources & evidence

ORD record
ord-80293863924d450ea4ea5615b68774d0
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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