Phosphorus tribromide → 1-(Bromomethyl)-2-fluoro-3-nitrobenzene
Reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:15]O>C(OCC)C>[Br:2][CH2:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[F:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of phosphorus tribromide (4.8 mL) in anhydrous diethylether (100 mL) was added at 0° C. to a solution of (2-fluoro-3-nitrophenyl)methanol (compound 2c-1) (7.52 g, 46.3 mmol) in anhydrous diethylether (130 mL), and the mixture was stirred at 30 minutes at 0° C. The reaction mixture was then poured into ice water and extracted with ethyl acetate. The organic extract was washed in series with saturated sodium hydrogen carbonate solution, water and saturated saline, and dried over magnesium sulfate. The title compound (7.10 g, 70%) was then obtained as a brown oil.
Workup
- extractionextracted with ethyl acetate
- extractionThe organic extract
- washwas washed in series with saturated sodium hydrogen carbonate solution, water and saturated saline
- dry with materialdried over magnesium sulfate
Sources & evidence
- ORD record
- ord-556711d65878497e8c6f0bfef069f595
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278465B2
Reaction notes
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