3,5-Dichloroaniline → 4-Bromo-3,5-dichloroaniline

3,5-Dichloroaniline (10 g, 61.7 mmol) in acetonitrile (100 mL) was taken in a 3-necked flask fitted with a thermometer, condenser and a dropping funnel containing N-bromosuccinimide (10.99 g, 61.7 mmol) in acetonitrile (30 mL). N-bromosuccinimide solution was added slowly to the 3,5-dichloroaniline solution in the flask at 0° C. by maintaining the internal temperature below 5° C. After the addition of NBS, the reaction mixture was warmed to RT and stirred for further 3 h. After the completion of the reaction as evidenced by LC-MS, the mixture was diluted with 10% aq. NaHSO3 (150 mL). The solution was stirred for 15 min and evaporated to ⅓ of the total volume of the solvents. The resultant mixture was then diluted with water and extracted with ethyl acetate. The organic solvent was dried, evaporated and purified by CombiFlash to give pure 4-bromo-3,5-dichloroaniline. Yield 13.6 g. 1H NMR (400 MHz; d6-DMSO): δ 5.82 (bs, 2H), 6.75 (s, 2H).

1. customfitted with a thermometer, condenser and a dropping funnel
2. temperatureby maintaining the internal temperature below 5° C
3. customAfter the completion of the reaction
4. stirringThe solution was stirred for 15 min
5. customevaporated
6. additionThe resultant mixture was then diluted with water
7. extractionextracted with ethyl acetate
8. customThe organic solvent was dried
9. customevaporated
10. custompurified by CombiFlash

ORD record

ord-b7f890c8e43245daa39391d95914cb82

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975254B2