4-Chlorobenzyl alcohol → 1-(Bromomethyl)-4-chlorobenzene

HRID 1720442Notes

Reaction equation

HRID 1720442 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:11]>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Br:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 133974-Chlorobenzyl alcoholHCID 24614Phosphorus tribromide

Product 1

HCID 693291-(Bromomethyl)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-chlorobenzyl alcohol (14.26 g, 100 mmol) in CH2Cl2 (40 mL) at ambient temperature was added added dropwise a solution of PBr3 in CH2Cl2 (1.0M, 32 mL, 32 mmol). The reaction mixture was stirred for 72 hours at ambient temperature and then was poured slowly onto ice. The layers were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-chlorobenzyl bromide (19.76 g) as a colorless solid.

Workup

  1. additionwas added
  2. additionwas poured slowly onto ice
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16e78c851b034b75b85895b9cee052a2
Source dataset
uspto-grants-1996_04
Patent number
US05506261

Reaction notes

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