3-(Phenylmethoxy)benzenemethanol → 3-Benzyloxybenzyl bromide

HRID 2394480Notes

Reaction equation

HRID 2394480 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[Si]([Br:21])(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 (9.54 g) in methylene chloride (40 ml) with TMSBr (2.5 eq, 13 mL) was heated at reflux for 1 hr. After cooling, the reaction was concentrated and then reconcentrated 2 × with methylene chloride (40 ml). The residue was chromatographed on silica gel eluting first with hexane followed by 10% methylene chloride in hexane to afford 3-benzyloxybenzyl bromide which solidifies on cooling . 5.75 g m.p. 38°-40°.

Workup

  1. temperatureat reflux for 1 hr
  2. temperatureAfter cooling
  3. concentrationthe reaction was concentrated
  4. customThe residue was chromatographed on silica gel eluting first with hexane

Sources & evidence

ORD record
ord-6cefe792b56e4ef6aa6f4e57ae107537
Source dataset
uspto-grants-1998_09
Patent number
US05811450

Reaction notes

Loading…