Phosphorus tribromide → 2-Bromo-4-(bromomethyl)-1-chlorobenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]O)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Br)(Br)[Br:12]>ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][Br:12])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
260 g (crude product of several batches, about 1.05 mol) of (3-bromo-4-chlorophenyl)methanol were dissolved in 2.86 liters of dichloromethane, the mixture was cooled to −5° C. and 127.1 g (44.6 ml, 459.6 mmol) of phosphorus tribromide were added slowly. After the addition had ended, the mixture was stirred at −5° C. for another 1 h and then diluted with dichloromethane and water. The organic phase was separated off, dried over magnesium sulphate and concentrated under reduced pressure. This gave, as a crude product, 280.5 g (about 84% of theory) of 2-bromo-4-(bromomethyl)-1-chlorobenzene.
Workup
- additionAfter the addition
- customThe organic phase was separated off
- dry with materialdried over magnesium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6468ed83fadf42b2b231799a257aa67f
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018258B2
Reaction notes
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