4-Bromo-2-(trifluoromethyl)aniline → HCID 86676831, compound

Temperature

0 °C

To 4-bromo-2-(trifluoromethyl)aniline (4.61 g, 19.21 mmol) in H2O (24 mL), conc. HCl (4 mL) was added and stirred at 0° C. for 10 min. NaNO2 (1.32 g, 19.21 mmol), dissolved in water (10 mL), was added to the reaction mixture and allowed to stir at 0° C. for 30 min. The solid obtained was filtered, the filtrate was cooled to 0° C. and 2-oxocyclohexanecarboxylic acid (2.46 g, 19.21 mmol) was added while maintaining the temperature at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for an additional 1 h. The solid obtained was filtered and air dried to afford the title compound (2 g, 30%). 1H NMR (200 MHz, CDCl3, δ in ppm) 14.05 (br s, 1H), 7.80-7.75 (d, J=8.8 Hz, 1H), 7.64-7.54 (m, 2H), 2.76-2.69 (m, 2H), 2.60-2.53 (m, 2H), 1.91-1.84 (m, 4H).

1. additionwas added to the reaction mixture
2. stirringto stir at 0° C. for 30 min
3. customThe solid obtained
4. filtrationwas filtered
5. temperaturethe filtrate was cooled to 0° C.
6. temperaturewhile maintaining the temperature at 0° C
7. temperatureThe reaction mixture was slowly warmed to room temperature
8. stirringstirred for an additional 1 h
9. customThe solid obtained
10. filtrationwas filtered
11. customair dried

ORD record

ord-778476c349c74fc5bb7fb260deeb19aa

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987319B2