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 into 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-part portions of toluene. The toluene extracts were combined and washed with four 300-part portions of water followed by 100-parts of saturated aqueous NaCl. The toluene solution of the product was dried over sodium sulfate and evaporated at a reduced pressure of 50 mm.Hg to give 2.6 parts of 4-amino-3-fluorobenzonitrile, 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-part portions of toluene
4. washwashed with four 300-part portions of water
5. dry with materialThe toluene solution of the product was dried over sodium sulfate
6. customevaporated at a reduced pressure of 50 mm.Hg

ORD record

ord-bdb8f411cebd4de8940bc2439d415e08

Source dataset

uspto-grants-1979_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04175948