Réaction #5772

Équation de réaction

4-nitroaniline

Thionyl chloride

2-bromobenzoic acid

→

2-bromo-N-(4-nitrophenyl)benzamide

Rendement 87.0%

Solvants

toluene

NMP

toluene

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was cooled to 20° C.
2. 2
   Températuremaintaining the temperature of the reaction mixture between 20°-25° C
3. 3
   Autreprecipitated
4. 4
   workup.ADDITIONWater (360 ml) was added
5. 5
   workup.STIRRINGwith rigorous stirring
6. 6
   Filtrationthe suspended solid collected by filtration
7. 7
   Lavagewashed successively with water, toluene and acetonitrile

Mode opératoire

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and N,N-dimethylformamide (DMF) (5 ml) and the mixture heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and NMP (120 ml), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours when a solid precipitated. Water (360 ml) was added with rigorous stirring and the suspended solid collected by filtration, and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide as a solid, in 87% yield, which was used without further purification or characterisation.

Source