Water → HCID 14100540, compound

2,3-Dichloro-5-(trifluoromethyl)pyridine (43.2 g, 0.20 mole) was dissolved in 140 g (1.17 mole) of chloroform and 105 g of N-methylpyrrolidone. Sodium hydroxide (40 g of 50 percent aqueous solution, 0.5 mole) was added with stirring and the mixture was allowed to stir for 20 hours at room temperature. Another 10 g of 50 percent aqueous sodium hydroxide was added and stirring was continued. After 27 total hours a large excess of water was added. The resulting aqueous layer was removed and the organic layer was concentrated on a rotary evaporator under reduced pressure to obtain an oil containing the title compound. The oil was distilled in a fractionating column and the product fractions washed with dilute aqueous sodium carbonate to obtain 18.8 g of the title compound (35.5 percent of theory) having 97 percent purity by gas chromatography. The product, which was identified by its mass spectrum (parent peak at 263 mass units) and gas chromatographic parameters (compared with an authentic standard), had a boiling point of 108°-114° C. at 19 mm Hg pressure. Approximately 17.5 g of unreacted 2,3-dichloro-5-(trifluoromethyl)pyridine was also recovered.

1. stirringto stir for 20 hours at room temperature
2. stirringstirring
3. customThe resulting aqueous layer was removed
4. concentrationthe organic layer was concentrated on a rotary evaporator under reduced pressure
5. customto obtain an oil

ORD record

ord-52be1d7d0bf74e86b388068af42b9e52

Source dataset

uspto-grants-1988_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04739070