Ammonia → 4-Bromo-3-chlorobenzamide

To a suspension of 4-bromo-3-chlorobenzoic acid (2.00 g, 8.49 mmol) in toluene (10 mL) at ambient temperature was added thionyl chloride (1.85 mL, 25.4 mmol). The reaction mixture was heated at reflux for 20.5 hours, then distilled for 1 hour, collecting 9 mL of distillate. Toluene (10 mL) was added and the reaction was distilled for 30 minutes, collecting 10 mL of distillate. The reaction mixture was cooled to ambient temperature resulting in a suspension. Toluene (10 mL) saturated with ammonia gas was added to the reaction mixture followed by bubbling ammonia gas through the reaction for 10 minutes. The reaction was stirred at ambient temperature for 1 hour. Heptane (10 mL) was added, and the reaction stirred at ambient temperature for 15 minutes, then 0° C. for 1 hour. The solids were collected by vacuum filtration, rinsed with excess heptane, and dried to afford 4-bromo-3-chlorobenzamide (2.327 g, 116.8%) as a white solid which was carried on without further purification.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 20.5 hours
3. distillationdistilled for 1 hour
4. distillationcollecting 9 mL of distillate
5. additionToluene (10 mL) was added
6. distillationthe reaction was distilled for 30 minutes
7. distillationcollecting 10 mL of distillate
8. customresulting in a suspension
9. customby bubbling ammonia gas
10. customthrough the reaction for 10 minutes
11. stirringthe reaction stirred at ambient temperature for 15 minutes
12. wait0° C. for 1 hour
13. filtrationThe solids were collected by vacuum filtration
14. washrinsed with excess heptane
15. customdried

ORDレコード

ord-0774f58a9c32486ba32f19e47168b60f

出典データセット

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08865726B2