تفاعل #1885032

معادلة التفاعل

sodium tetrafluoroborate

4-chloro-3-methylaniline

HCl

sodium nitrite

→

4-chloro-3-methylbenzenediazonium tetrafluoroborate

المردود 95.2%

المذيبات

water

water

water

ظروف التفاعل

المعالجة

1. 1
   أخرىSynthesized
2. 2
   workup.ADDITIONwas added in one portion
3. 3
   ترشيحThe solid was filtered
4. 4
   غسيلwashed with cold (5° C.) diethyl ether (10 mL)
5. 5
   workup.DISSOLUTIONThe solid was dissolved in acetone (15 mL)
6. 6
   ترشيحfiltered
7. 7
   workup.ADDITIONTo the filtrate was added diethyl ether (15 mL)
8. 8
   أخرىthe precipitation of the arenediazonium tetrafluoroborate
9. 9
   ترشيحThe solid was filtered
10. 10
    غسيلwashed with cold (5° C.) diethyl ether (5 mL)
11. 11
    أخرىair dried overnight

الإجراء التجريبي

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.

المصدر