Reaction #452423

Reaction equation

water

4-fluorobenzoyl chloride

4-nitroaniline

pyridine

→

N-(4-fluorobenzoyl)-4-nitroaniline

Yield 91.3%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.WAITfor an hour at room temperature
2. 2
   Otherthe solid which formed
3. 3
   Filtrationwas collected by filtration
4. 4
   WashThe filter cake was washed with hexane (80 mL)
5. 5
   Otherwas then dried under vacuum at 60° C.

Procedure

To a stirred suspension of 19.83 gm (143.56 mMol) 4-nitroaniline in 150 mL dichloromethane and 12.9 mL (159.5 mMol) pyridine at 0° C. were slowly added 24.5 gm (154.8 mMol) 4-fluorobenzoyl chloride. The reaction mixture was then stirred for 15 minutes at 0° C., at which time the reaction mixture became homogeneous, and then for an hour at room temperature. To this mixture were then added 100 mL water and the solid which formed was collected by filtration. The filter cake was washed with hexane (80 mL) followed by water (100 mL) and it was then dried under vacuum at 60° C. to give 34.1 gm (91%) N-(4-fluorobenzoyl)-4-nitroaniline.

Source