Hydrochloric Acid → 2-Chloro-4-(trifluoromethoxy)benzonitrile

An aqueous solution of 2-chloro-4-(trifluoromethoxy)phenylamine (9.0 g) was cooled at 0° C., and concentrated hydrochloric acid (75 mL) was dropped slowly to its solution. The reaction mixture was stirred for 30 minutes, and sodium nitrite (3.73 g) was added to the reaction mixture. The reaction mixture was stirred for 40 minutes. An aqueous mixture solution of copper cyanide (4.65 g) and sodium cyanide (7.08 g) which been cooled off in 0° C. was added to the reaction mixture, and the reaction mixture stirred at room temperature for an hour. The reaction mixture was poured into 5N aqueous solution of sodium hydroxide which been cooled with ice, and extracted twice with ethyl acetate. The organic layer was washed by a saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (high flash-SI, size 4 L (made in Yamazen corporation), n-hexane→ethyl acetate/n-hexane=1/8) to obtain a title compound (7.36 g) having the following physical data.

1. stirringThe reaction mixture was stirred for 40 minutes
2. additionwas added to the reaction mixture
3. stirringthe reaction mixture stirred at room temperature for an hour
4. temperaturebeen cooled with ice
5. extractionextracted twice with ethyl acetate
6. washThe organic layer was washed by a saturated aqueous solution of sodium chloride
7. dry with materialdried with anhydrous sodium sulfate
8. concentrationThe organic layer was concentrated under reduced pressure
9. customThe obtained residue was purified by column chromatography on silica gel (high flash-SI, size 4 L (made in Yamazen corporation), n-hexane→ethyl acetate/n-hexane=1/8)

ORD record

ord-ffb4a4c2f1d1468cba0f9157ad35d03f

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420810B2