Phosphorus tribromide → 1-(Bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[Br:19][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Procedure
To a solution of {4-chloro-2-[(phenylmethyl)oxy]phenyl}methanol (for as preparation see Intermediate 15) (0.501 g, 2.02 mmol) in DCM (10 ml) at −10 to −15° C., under nitrogen, was added a solution of phosphorus tribromide (0.190 ml, 2.02 mmol, Aldrich) in DCM (5 ml) dropwise. The solution was allowed to warm to ambient temperature and stirred for 4.5 h. To the reaction mixture in an ice-water bath was added dropwise saturated aqueous sodium hydrogen carbonate (5 ml). The mixture was diluted with water (45 ml) and dichloromethane (55 ml). The phases were separated and the aqueous phase washed with DCM (30 ml). The combined organic extracts were washed with water (10 ml). The organic extract was dried (MgSO4), filtered and the solvent removed in vacuo to give 1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene as a colourless gum (0.505 g).
Workup
- customThe phases were separated
- washthe aqueous phase washed with DCM (30 ml)
- washThe combined organic extracts were washed with water (10 ml)
- extractionThe organic extract
- dry with materialwas dried (MgSO4)
- filtrationfiltered
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-941febf977da4793924e982431ad965a
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
Loading…