Reaction #172381

Reaction equation

3-bromopyridin-2(1H)-one

potassium tert-butoxide

1-fluoro-2-methyl-4-nitrobenzene

→

3-Bromo-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

Solvents

dimethyl sulphoxide

water

Conditions

Workup

1. 1
   Temperatureto cool
2. 2
   FiltrationThe resulting crystalline precipitate is filtered off
3. 3
   Washwashed with a little water
4. 4
   Otherdried under reduced pressure

Procedure

44.5 g (280 mmol) of 3-bromopyridin-2(1H)-one are dissolved in 750 ml of anhydrous dimethyl sulphoxide, and 33.4 g (298 mmol) of potassium tert-butoxide are added a little at a time at room temperature. The suspension is stirred at this temperature for 1 h, 38.5 g (280 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are then added and the reaction solution is heated at 80° C. for 20 h. The solution is allowed to cool and carefully diluted with water. The resulting crystalline precipitate is filtered off, washed with a little water and dried under reduced pressure. This gives 62 g (80% of theory) of the desired product.

Source