Reacción #1885032

Ecuación de reacción

sodium tetrafluoroborate

4-chloro-3-methylaniline

HCl

sodium nitrite

→

4-chloro-3-methylbenzenediazonium tetrafluoroborate

Rendimiento 95.2%

Disolventes

water

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSynthesized
2. 2
   workup.ADDITIONwas added in one portion
3. 3
   FiltraciónThe solid was filtered
4. 4
   Lavadowashed with cold (5° C.) diethyl ether (10 mL)
5. 5
   workup.DISSOLUTIONThe solid was dissolved in acetone (15 mL)
6. 6
   Filtraciónfiltered
7. 7
   workup.ADDITIONTo the filtrate was added diethyl ether (15 mL)
8. 8
   Otrothe precipitation of the arenediazonium tetrafluoroborate
9. 9
   FiltraciónThe solid was filtered
10. 10
    Lavadowashed with cold (5° C.) diethyl ether (5 mL)
11. 11
    Otroair dried overnight

Procedimiento

Synthesized according to General Procedure 1. 4-chloro-3-methylaniline (5 g, 35.3 mmol) in water (15 mL) and conc. HCl (9.5 mL, 116.5 mmol) at −5° C. was added a freshly prepared aqueous solution of sodium nitrite (3.2 g, 45.9 mmol) in water (8 mL) slowly over 10 minutes. After stirring for 15 minutes at −5° C. a freshly prepared aqueous solution of sodium tetrafluoroborate (5.4 g, 49.4 mmol) in water (14 mL) was added in one portion causing the formation of a precipitate. The solid was filtered and washed with cold (5° C.) diethyl ether (10 mL). The solid was dissolved in acetone (15 mL) and filtered. To the filtrate was added diethyl ether (15 mL) causing the precipitation of the arenediazonium tetrafluoroborate. The solid was filtered, washed with cold (5° C.) diethyl ether (5 mL) and then air dried overnight to provide 4-chloro-3-methylbenzenediazonium tetrafluoroborate (8.07 g, 33.6 mmol, 95% yield) as a tan solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.68 (d, J=2.2 Hz, 1H), 8.56 (dd, J=2.4, 8.8 Hz, 1H), 8.10 (d, J=8.8 Hz, 1H) and 3.47 (s, 3H) ppm. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=125.0; tR=0.24 min.

Fuente