Phosphorus oxychloride → Methyl 5-bromo-6-chloropicolinate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([O:11][CH3:12])=[O:10])=[N+:6]([O-])[CH:7]=1.P(Cl)(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([O:11][CH3:12])=[O:10])=[N:6][C:7]=1[Cl:15]Participants
3
Conditions
- Temperature
- 90 °C
Procedure
To 5-bromo-2-(methoxycarbonyl)pyridine 1-oxide (22.0 g) was added phosphoryl chloride (40.0 mL), and the mixture was stirred at 90° C. for 10 min. The reaction mixture was cooled to room temperature and poured into ice water. The mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (16.0 g) as a white amorphous solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionThe mixture was extracted with ethyl acetate
- washthe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a3f83a0980f149db8a12b475c50213af
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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