Reacción #1888909

Ecuación de reacción

1-bromo-5-methyl-2-nitro-4-trifluoromethyl-benzene

1-Bromo-5-methyl-2-nitro-4-trifluoromethyl-benzene

copper(I) cyanide

HCl

→

title compound

Rendimiento 88.1%

5-Methyl-2-nitro-4-trifluoromethyl-benzonitrile

Rendimiento 88.1%

Disolventes

1-methyl-2-pyrrolidone

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to 23° C.
2. 2
   Extracciónextracted with TBME
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over Na2SO4
5. 5
   OtroRemoval of the solvent in vacuum
6. 6
   workup.WAITleft a brown oil, which
7. 7
   Otrowas purified by silica gel column chromatography with heptane/ethyl acetate 4:1→2:1

Procedimiento

A mixture of 1-bromo-5-methyl-2-nitro-4-trifluoromethyl-benzene from step 2 (49.80 g, 175 mmol) and copper(I) cyanide (16.5 g, 184 mmol) in 1-methyl-2-pyrrolidone (NMP) (180 mL) was heated up to 150° C. and stirred for 30 min under nitrogen atmosphere. The mixture was cooled to 23° C. and poured into 1 N HCl, extracted with TBME, washed with brine and dried over Na2SO4. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with heptane/ethyl acetate 4:1→2:1 to give the title compound as a light yellow solid (35.48 g, 88%). MS (EI) 230.1 [M].

Fuente