Reaction #84424

Reaction equation

3,4-difluoronitrobenzene

K2CO3

di-n-hexylamine

→

title compound

Yield 86.0%

2-fluoro-N,N-di-n-hexyl-4-nitroaniline

Yield 86.0%

Solvents

DMSO

water

Conditions

Workup

1. 1
   Temperaturecooled to rt
2. 2
   Extractionextracted with CH2Cl2 (50 mL×3)
3. 3
   DryingThe combined organic phases were dried over anhydrous Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=10:1)

Procedure

To a solution of 3,4-difluoronitrobenzene (1.59 g, 10 mmol) in DMSO (15 mL) were added K2CO3 (3.04 g, 22 mmol) and di-n-hexylamine (2.04 g, 11 mmol). The mixture was heated at 90° C. overnight, then cooled to rt, diluted with water (50 mL) and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=10:1) to give the title compound as pale yellow oil (2.79 g, 86%).

Source