Benzyl Bromide → 1-(Benzyloxy)-2-bromo-4-chlorobenzene

HRID 16075

Reaction equation

HRID 16075 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 115511251-(Benzyloxy)-2-bromo-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (13.1 ml) was added to a stirred mixture of 2-bromo-4-chlorophenol (20.7 g) and potassium carbonate (27.6 g) in DMF (200 ml). After 72 h, the mixture was partitioned between diethylether and water, the organic layer washed with water, dried and the solvent evaporated under reduced pressure. The residue was purified by chromatography (silica, EtOAc/isohexane as eluent). to give the sub-title compound (18.1 g).

Workup

  1. customthe mixture was partitioned between diethylether and water
  2. washthe organic layer washed with water
  3. customdried
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by chromatography (silica, EtOAc/isohexane as eluent)

Sources & evidence

ORD record
ord-271c6ca507864f3b817771dbfa8e87fb
Source dataset
uspto-grants-2010_06
Patent number
US07737135B2

Linked notes

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