Sodium Cyanide → 4-Amino-3-fluorobenzonitrile

6.8 Parts of 4-bromo-2-fluoroaniline were dissolved in 75 parts of N-methylpyrrolidone. This solution was treated with 4.2 parts of cuprous cyanide. The reaction mixture was heated to 190° for 2 hours. The reaction mass was poured onto a mixture of 200 parts of ice and 15 parts of sodium cyanide. This mixture was then heated on a steam bath for 2 hours at 60°-70°. This aqueous solution was then extracted with four 100 ml portions of toluene. The toluene extracts were combined and washed with four 300 ml portions of water followed by 100 ml of saturated aqueous NaCl solution. The toluene solution of the product was dried over sodium sulfate and stripped to give 2.6 parts of the desired product, m.p. 71°-73°.

1. temperatureThe reaction mixture was heated to 190° for 2 hours
2. temperatureThis mixture was then heated on a steam bath for 2 hours at 60°-70°
3. extractionThis aqueous solution was then extracted with four 100 ml portions of toluene
4. washwashed with four 300 ml portions of water
5. dry with materialThe toluene solution of the product was dried over sodium sulfate

ORD record

ord-2de4be99b6ff4d9b8994f6dbf257aba4

Source dataset

uspto-grants-1978_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04111681