Carbon tetrabromide → 3-Benzyloxybenzyl bromide

HRID 1993131Notes

Reaction equation

HRID 1993131 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[CH2:25]([O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)CO)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:25]([O:32][C:33]1[CH:40]=[C:39]([CH:38]=[CH:35][CH:34]=1)[CH2:20][Br:24])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

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

Product 1

HCID 15020473-Benzyloxybenzyl bromideYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenyl phosphine (15.7 g, 60 mmol) in THF (150 mL) was added a solution of carbon tetrabromide (20 g, 60 mmol) in THF (50 mL). A precipitation was formed and stirred for 10 min. A solution of 3-benzyloxybenzyl alcohol 50.4 (10 g, 46.7 mmol) was added. After stirred for 1.5 h, the reaction mixture was filtered and concentrated under reduced pressure. The majority of triphenyl phosphine oxide was removed by precipitation from ethyl acetate-hexane. The crude product was purified by chromatography on silica gel and precipitation from hexane to give the desired product 3-Benzyloxybenzylbromide 6.9 (10 g, 77%) as a white solid.

Workup

  1. customA precipitation
  2. customwas formed
  3. stirringAfter stirred for 1.5 h
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe majority of triphenyl phosphine oxide was removed by precipitation from ethyl acetate-hexane
  7. customThe crude product was purified by chromatography on silica gel and precipitation from hexane

Sources & evidence

ORD record
ord-4fa70b3cc2704dd3b250bf41ab18b149
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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