Ethanol → 1-(Benzyloxy)-2-bromobenzene

HRID 1608479Notes

Reaction equation

HRID 1608479 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].C(O)C.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)C>[CH2:14]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 72442-BromophenolHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a three-necked flask of one liter, 25g (0.145 mol) of o-bromophenol, 8.7 g (0.217 mol) of sodium hydroxide and 300 ml of ethanol were charged and refluxed for two hours. Then, 49.4 g (0,289 mol) of benzyl bromide was added dropwise and the mixture was refluxed further for four hours. After the mixture was cooled to room temperature, 600 ml of diethyl ether was added. The mixture was charged into a separatory funnel. Separated organic layer was washed successively with, 100 ml of 2N-hydrochloric acid cooled with ice, 300 ml of saturated sodium thiosulfate, and water until the washings were neutral. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The concentrate was distilled under reduced pressure to obtain 35.6 g (0.135 mol) of o-benzyloxyphenylbromide.

Workup

  1. temperaturerefluxed for two hours
  2. temperaturethe mixture was refluxed further for four hours
  3. additionThe mixture was charged into a separatory funnel
  4. washSeparated organic layer was washed successively with, 100 ml of 2N-hydrochloric acid
  5. temperaturecooled with ice, 300 ml of saturated sodium thiosulfate, and water until the washings
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. distillationThe concentrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-482e5a4fc7ed41cd9299752397d95021
Source dataset
uspto-grants-1995_03
Patent number
US05395766

Reaction notes

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