Hydrochloric Acid → 4-Chloro-3-methylbenzenediazonium tetrafluoroborate

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.

1. customSynthesized
2. additionwas added in one portion
3. filtrationThe solid was filtered
4. washwashed with cold (5° C.) diethyl ether (10 mL)
5. dissolutionThe solid was dissolved in acetone (15 mL)
6. filtrationfiltered
7. additionTo the filtrate was added diethyl ether (15 mL)
8. customthe precipitation of the arenediazonium tetrafluoroborate
9. filtrationThe solid was filtered
10. washwashed with cold (5° C.) diethyl ether (5 mL)
11. customair dried overnight

ORD-Eintrag

ord-20f720dea6e94d35bd75d164cc22b347

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08143297B2