Reacción #78085

Ecuación de reacción

sodium nitrite

hydrochloric acid

4-t-butylaniline

sodium tetrafluoroborate

→

1f

Rendimiento 73.5%

4-Fluoro-3-nitro-t-butylbenzene

Rendimiento 73.5%

Disolventes

water

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 5-7° C
2. 2
   workup.ADDITIONAt the end of the addition
3. 3
   workup.ADDITIONwas added dropwise
4. 4
   FiltraciónAfter another 15 min at 5° C. the diazonium salt was filtered off
5. 5
   Otrodried with suction
6. 6
   Lavadowashed with diethyl ether (yield: 21 g)
7. 7
   Temperaturaby gentle heating to 120° C. on an oil-bath
8. 8
   workup.DISTILLATIONThe product was distilled off
9. 9
   Otrocollected

Procedimiento

To a cold (5° C.) suspension of 4-t-butylaniline in a mixture of conc. hydrochloric acid (25 ml) and water (25 ml) was added a solution of sodium nitrite (7.6 g, 0.11 mol) in water (10 ml) keeping the temperature at 5-7° C. At the end of the addition, the mixture was stirred for additionally 15 min, whereafter a solution of sodium tetrafluoroborate (15.4 g, 0.14 mol) in water (30 ml) was added dropwise, maintaining the temperature at 5-8° C. After another 15 min at 5° C. the diazonium salt was filtered off, dried with suction and washed with diethyl ether (yield: 21 g). The diazonium salt was decomposed by gentle heating to 120° C. on an oil-bath. The product was distilled off and collected to yield 1f (11.2 g, 73.5%).

Fuente