Phosphorus oxychloride → Methyl 5-bromo-6-chloropicolinate

Temperature

90 °C

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 reaction 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. This compound was used for the next step without further purification.

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washthe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure

ORD record

ord-40b814f424b6490187514f060fde7d79

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181186B2