Water → 4-Bromo-2-(bromomethyl)-1-chlorobenzene

HRID 427252Notes

Reaction equation

HRID 427252 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7]O.P(Br)(Br)[Br:12].O>COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][Br:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzeneYield 252.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

20.0 g of 5-bromo-2-chlorobenzyl alcohol was dissolved in 100 ml of ethylene glycol dimethyl ether. To this solution, 9.4 g of phosphorus tribromide was added at −20° C., followed by stirring at room temperature for 1 hour. To the reaction solution, water was added, followed by extraction with toluene, and washing with an aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 24.9 g of a crude product of 5-bromo-2-chlorobenzyl bromide as white crystals.

Workup

  1. extractionfollowed by extraction with toluene
  2. washwashing with an aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d11603a1c87b493191c98e110d8eef3d
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Reaction notes

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