3-(Phenylmethoxy)benzenemethanol → 3-Benzyloxybenzyl bromide

HRID 725022

Reaction equation

HRID 725022 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.[Si]([Br:21])(C)(C)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][Br:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 743413-(Phenylmethoxy)benzenemethanolHCID 76113Bromotrimethylsilane

Product 1

HCID 15020473-Benzyloxybenzyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-benzyloxybenzyl alcohol (2.04 g) in methylene chloride (20 mL) with TMS Bromide (2.5 eq. 3.14 mL) was heated at reflux for 6 hr. After cooling, the reaction was concentrated and then reconcentrated 2× from methylene chloride. The residue was chromatographed on silica gel with 5% methylene chloride in hexane to afford 3-benzyloxybenzyl bromide (1.26 g) as an oil.

Workup

  1. temperatureat reflux for 6 hr
  2. temperatureAfter cooling
  3. concentrationthe reaction was concentrated
  4. customThe residue was chromatographed on silica gel with 5% methylene chloride in hexane

Sources & evidence

ORD record
ord-148bdd1a9f154f59962ee4b9f4440268
Source dataset
uspto-grants-1998_01
Patent number
US05705524

Linked notes

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