Phosphorus tribromide → 1-(Bromomethyl)-2,4-dimethylbenzene
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:9]O.P(Br)(Br)[Br:12]>CCOCC>[Br:12][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5 g of (2,4-dimethylphenyl)methanol are dissolved in 100 ml of ether. The reaction mixture is cooled to 0° C. It is admixed dropwise with 5.2 ml of phosphorus tribromide. It is stirred at ambient temperature overnight. The reaction mixture is poured onto ice and extracted with AcOEt. The organic phase is washed with saturated NaCl solution. The organic phase is dried over MgSO4, filtered and evaporated to dryness. This gives 7.3 g of the expected compound.
Workup
- additionThe reaction mixture is poured onto ice
- extractionextracted with AcOEt
- washThe organic phase is washed with saturated NaCl solution
- dry with materialThe organic phase is dried over MgSO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-d73d118dd0614b2d8413423dd397717a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812165B2
Reaction notes
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