Carbon tetrabromide → 3-Benzyloxybenzyl bromide

HRID 2243798Notes

Reaction equation

HRID 2243798 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:18][CH2:12][C:11]1[CH:10]=[C:9]([CH:16]=[CH:15][CH:14]=1)[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 743413-(Phenylmethoxy)benzenemethanol

Product 1

HCID 15020473-Benzyloxybenzyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-benzyloxybenzyl alcohol (2 g, 9.3 mmol) and carbon tetrabromide (4 g, 12.1 mmol) in CH2Cl2 (70 mL), cooled to 0° C., was added a solution of triphenylphosphine (2.9 g, 11.2 mmol) in CH2Cl2 (20 mL). The reaction was stirred at rt for 3 h and concentrated. Purification by flash chromatography (silica gel, 0-8% EtOAc/hexanes) gave 1-((3-(bromomethyl)phenoxy)methyl)benzene. 1H NMR (400 MHz, CDCl3) δ 7.39 (m, 5H), 7.25 (m, 1H), 7.00 (m, 2H), 6.92 (m, 1H), 5.06 (s, 2H), 4.46 (s, 2H).

Workup

  1. concentrationconcentrated
  2. customPurification by flash chromatography (silica gel, 0-8% EtOAc/hexanes)

Sources & evidence

ORD record
ord-94e135cb51e54bf1af9815725d1c0dfb
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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