Reaction #470392

Reaction equation

2,6-diisopropylaniline

2-fluoronitrobenzene

potassium fluoride

→

desired product

Yield 47.9%

2,6-diisopropyl-N-(2-nitrophenyl)aniline

Yield 47.9%

Solvents

water

Conditions

Workup

1. 1
   TemperatureAfter cooled to room temperature
2. 2
   ExtractionThe mixture was then extracted with dichloromethane (200 mL) for three times
3. 3
   OtherThe solvent was evaporated
4. 4
   Otherthe residue was purified by column chromatography

Procedure

2,6-diisopropylaniline (25 g, 141 mmol), 2-fluoronitrobenzene (10 g, 70 mmol), and potassium fluoride (6.2 g, 106 mmol) were mixed in a one-neck flask. The mixture was heated up to 180° C. under nitrogen for 48 hours. After cooled to room temperature, water (200 mL) was added. The mixture was then extracted with dichloromethane (200 mL) for three times. The solvent was evaporated and the residue was purified by column chromatography using 20% of dichloromethane in hexanes. 10 g of desired product was obtained.

Source