反応 #1885032

反応方程式

sodium tetrafluoroborate

4-chloro-3-methylaniline

HCl

sodium nitrite

→

4-chloro-3-methylbenzenediazonium tetrafluoroborate

収率 95.2%

溶媒

water

water

water

反応条件

後処理

1. 1
   その他Synthesized
2. 2
   workup.ADDITIONwas added in one portion
3. 3
   ろ過The solid was filtered
4. 4
   洗浄washed with cold (5° C.) diethyl ether (10 mL)
5. 5
   workup.DISSOLUTIONThe solid was dissolved in acetone (15 mL)
6. 6
   ろ過filtered
7. 7
   workup.ADDITIONTo the filtrate was added diethyl ether (15 mL)
8. 8
   その他the precipitation of the arenediazonium tetrafluoroborate
9. 9
   ろ過The solid was filtered
10. 10
    洗浄washed with cold (5° C.) diethyl ether (5 mL)
11. 11
    その他air dried overnight

実験手順

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.

出典