Phosphorus tribromide → 1-(Bromomethyl)-2-methanesulfonylbenzene
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11]O)(=[O:4])=[O:3].P(Br)(Br)[Br:14]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:14][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[S:2]([CH3:1])(=[O:4])=[O:3]Participants
5
Procedure
To a stirred solution of (2-methanesulfonyl-phenyl)methanol (735 mg, 3.99 mmol) in dry DCM (2 mL) at 0° C., add a solution of 1M phosphorous tribromide in DCM (6.0 mL, 6.0 mmol) and continue stirring for 1 h. Dilute with saturated aqueous NaHCO3, extract three times with ethyl ether, dry over anhydrous MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (12:1) to provide the title compound as a white solid (950 mg, 97%).
Workup
- extractionextract three times with ethyl ether
- dry with materialdry over anhydrous MgSO4
- concentrationconcentrate in vacuo
- customPurify by chromatography on silica gel eluting with hexane/EtOAc (12:1)
Sources & evidence
- ORD record
- ord-f79206e862aa4842a06435b8aa4432e0
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022062B2
Reaction notes
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