Phosphorus tribromide → 4-Bromo-2-(bromomethyl)-1-fluorobenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:8]O)[CH:7]=1.P(Br)(Br)[Br:12].C([O-])(O)=O.[Na+]>COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:8][Br:12])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To (5-bromo-2-fluoro-phenyl)-methanol (1.2 g, 5.9 mmol) in DME (20 mL) was added phosphorus tribromide (0.83 mL, 8.8 mmol), and the reaction was stirred at room temperature for 6 hours. The mixture was cooled to 0° C. and adjusted to pH 6 with saturated aqueous NaHCO3. The solution was extracted with EtOAc, and the combined organic layers were dried, concentrated, and purified by silica gel chromatography to give the title compound.
Workup
- temperatureThe mixture was cooled to 0° C.
- extractionThe solution was extracted with EtOAc
- customthe combined organic layers were dried
- concentrationconcentrated
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-81d61cfb8f294986860eb236a730ea7e
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067445B2
Reaction notes
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