Phosphorus tribromide → 1-(Bromomethyl)-2,3-dichlorobenzene
Reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9]O.[Br:11]P(Br)Br>C1(C)C=CC=CC=1>[Br:11][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2,3-dichlorophenyl)methanol (75 g, 0.431 mol), in toluene (800 mL), tribromophosphine (40.7 g, 0.151 mol) was added dropwise at room temperature with stirring. Then the reaction mixture was stirred at room temperature for 2 h and concentrated. The resulting residue was neutralized with aq. NaHCO3 and extracted with DCM (300 mL*3). The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (84.7 g, 83%), as a deep red solid.
Workup
- stirringThen the reaction mixture was stirred at room temperature for 2 h
- concentrationconcentrated
- extractionextracted with DCM (300 mL*3)
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-e48f5f36a4ef4f608eefac9d6c4f6b53
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096605B2
Reaction notes
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