Phosphorus oxybromide → 4-Bromo-1-(bromomethyl)-2-(methanesulfonyl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.P(Br)(Br)([Br:16])=O.P(Br)(Br)Br>[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:16])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1Participants
5
Conditions
- Temperature
- 130 °C
Procedure
To a solution of (4-bromo-2-methanesulfonyl-phenyl)-methanol (preparation 112) (100 mg, 0.38 mmol) in POBr3 (542 mg, 1.89 mmol) was added PBr3 (511 mg, 1.89 mmol). After the addition, the reaction mixture was stirred at 130° C. overnight. TLC (petroleum ether:EtOAc 1:1) showed the reaction was complete. The reaction was cooled to room temperature and then poured into brine (10 mL) and extracted with EtOAc (10 mL×2). The combined organic layers were washed with brine (10 mL×2), dried over sodium sulfate and concentrated in vacuo to give crude 4-bromo-1-bromomethyl-2-methanesulfonyl-benzene (200 mg, 80%) as a white solid.
Workup
- additionAfter the addition
- temperatureThe reaction was cooled to room temperature
- extractionextracted with EtOAc (10 mL×2)
- washThe combined organic layers were washed with brine (10 mL×2)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0a6ca641ef8647719cfa6bd1eb36e776
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916593B2
Reaction notes
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