4-Chlorobenzyl alcohol → 1-(Bromomethyl)-4-chlorobenzene
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- additionwas added
- additionwas poured slowly onto ice
- customThe layers were separated
- dry with materialthe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b84de76bff364798be1a6cb094b81efd
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616596
Reaction notes
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