Phosphorus tribromide → 1-(Bromomethyl)-2-chloro-4-[(phenylmethyl)oxy]benzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:16]O.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:19][CH2:16][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:2]=1[Cl:1]Participants
Procedure
To a solution of {2-chloro-4-[(phenylmethyl)oxy]phenyl}methanol (2.08 g, 8.36 mmol) in DCM (20 ml) under nitrogen in an ice-water bath was added a solution of phosphorus tribromide (0.83 ml, 8.80 mmol, Aldrich) in DCM (10 ml). The solution was allowed to warm to ambient temperature and stirred for 1.5 h. The reaction mixture was poured onto ice-water (70 ml) and saturated aqueous sodium hydrogen carbonate (30 ml). The mixture was diluted with DCM (50 ml), and the phases separated. The aqueous extract was washed with dichloromethane (20 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give 1-(bromomethyl)-2-chloro-4-[(phenylmethyl)oxy]benzene as white solid (2.48 g).
Workup
- customthe phases separated
- extractionThe aqueous extract
- washwas washed with dichloromethane (20 ml)
- washThe combined organic extracts were washed with water (50 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-1cffec4b81194c34ac8ec5ba08885e9c
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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