Réaction #339038

Équation de réaction

4-bromo-4-chlorobenzonitrile

hydrochloric acid

sodium hydroxide

→

product

4-Bromo-2-chlorobenzylamine hydrochloride

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autre46.2 ml of borane-THF complex are provided under ice cooling
2. 2
   TempératureThe reaction mixture is then heated for 1 h
3. 3
   Températureunder reflux
4. 4
   Températurecooled
5. 5
   Températurewhile cooling on ice
6. 6
   TempératureThe mixture is heated
7. 7
   Températureunder reflux for 1 h
8. 8
   workup.WAITleft
9. 9
   Températureto cool
10. 10
    Extractionextracted with dichloromethane
11. 11
    SéchageThe organic phase is dried over sodium sulfate
12. 12
    Concentrationconcentrated on a rotary evaporator
13. 13
    workup.ADDITION6 ml of hydrochloric acid in dioxane (4N) are added
14. 14
    Filtrationthe precipitated hydrochloride is collected by suction filtration

Mode opératoire

46.2 ml of borane-THF complex are provided under ice cooling. A solution of 2.0 g of 4-bromo-4-chlorobenzonitrile in 240 ml of THF is added slowly. The reaction mixture is then heated for 1 h under reflux, cooled and 20 ml of 1N hydrochloric acid are added dropwise while cooling on ice. The mixture is heated under reflux for 1 h and left to cool. For the work-up the solution is adjusted to an alkaline pH with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. 6 ml of hydrochloric acid in dioxane (4N) are added and the precipitated hydrochloride is collected by suction filtration. 1.3 g of product are obtained.

Source