반응 #1885032

반응 방정식

sodium tetrafluoroborate

4-chloro-3-methylaniline

HCl

sodium nitrite

→

4-chloro-3-methylbenzenediazonium tetrafluoroborate

수율 95.2%

용매

water

water

water

반응 조건

후처리

1. 1
   기타Synthesized
2. 2
   workup.ADDITIONwas added in one portion
3. 3
   여과The solid was filtered
4. 4
   세척washed with cold (5° C.) diethyl ether (10 mL)
5. 5
   workup.DISSOLUTIONThe solid was dissolved in acetone (15 mL)
6. 6
   여과filtered
7. 7
   workup.ADDITIONTo the filtrate was added diethyl ether (15 mL)
8. 8
   기타the precipitation of the arenediazonium tetrafluoroborate
9. 9
   여과The solid was filtered
10. 10
    세척washed with cold (5° C.) diethyl ether (5 mL)
11. 11
    기타air dried overnight

실험 절차

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.

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