2-Chloro-5-bromoaniline → 1067197-15-2

Temperature

5 °C

A suspension of 5-bromo-2-chloroaniline (23 g, 0.11 mol) in concentrated hydrochloric acid (150 mL) and water (90 mL) was cooled in an ice/salt bath. A solution of sodium nitrite (8 g, 0.11 mol) in water (50 mL) was added dropwise to the reaction mixture while maintaining the temperature below 4° C. After stirring for 30 minutes the suspension was transferred via cannula to a solution of SnCl2 dihydrate in concentrated hydrochloric acid (170 mL) and cooled to 5° C. The resulting thick suspension was stirred for 2 h at 5° C. and the solid was isolated via filtration. The solid was air dried and then further dried by adding chlorobutane (500 mL) and refluxing using a Dean-Stark condenser. After cooling, the solid was isolated by filtration to afford the title compound as an off-white solid (35.3 g). 1H NMR (CD3COCD3): δ 10.25 (br s, 1H), 8.32 (br s, 2H) 7.38 (d, 1H), 7.30 (d, 1H), 7.16 (dd, 1H).

1. temperaturewas cooled in an ice/salt bath
2. temperaturewhile maintaining the temperature below 4° C
3. stirringThe resulting thick suspension was stirred for 2 h at 5° C.
4. customthe solid was isolated via filtration
5. customdried
6. customfurther dried
7. additionby adding chlorobutane (500 mL)
8. temperaturerefluxing
9. temperatureAfter cooling
10. customthe solid was isolated by filtration

ORD record

ord-eadaa1ad82b84de1818d0a998748f6e7

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09198433B2