Benzyl Chloride → 1-Bromo-4-phenylmethoxybenzene

HRID 1936332Notes

Reaction equation

HRID 1936332 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 58.07%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

First, 53.2 g of benzyl chloride, 69.2 g of 4-bromophenol, 110.4 g of potassium carbonate, and 800 ml of methyl ethyl ketone were put in a 2 flask, and stirred under reflux for 30 minutes. After the reaction, insoluble material was filtered off, and the solvent was distilled off from the filtrate. Ether and a 2% sodium hydroxide aqueous solution were added to the residue to separate an organic layer. The organic layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was distilled (b.p. 131° C. to 140° C./0.08 mmHg), to obtain 61.0 g (Y: 58.07%) of 4-bromo-1-benzyloxybenzene. The purity of the resultant compound was 99.0% as measured by GC.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customAfter the reaction, insoluble material
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off from the filtrate
  5. additionEther and a 2% sodium hydroxide aqueous solution were added to the residue
  6. customto separate an organic layer
  7. washThe organic layer was washed with a saturated brine
  8. dry with materialdried with sodium sulfate
  9. distillationThe solvent was then distilled off
  10. distillationThe residue was distilled (b.p. 131° C. to 140° C./0.08 mmHg)

Sources & evidence

ORD record
ord-83ce407ac1ab4e07a1ccf674084f03f4
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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