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

HRID 1023769Notes

Reaction equation

HRID 1023769 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-48fa6ee028ab4ecea3f6b6265a983236
Source dataset
uspto-grants-2014_05
Patent number
US08722741B2

Reaction notes

Loading…