N-bromobutanimide → HCID 86714618, compound

Temperature

0 °C

2-Chloro-3,6-difluoroaniline (18.34 mmol, 3 g) was dissolved in ACN and cooled to 0° C. with an ice bath. A solution of N-bromosuccinimide (18.34 mmol, 3.26 g) dissolved in ACN was added using a dropping funnel maintaining the internal temperature of the reaction mixture below 5° C. After addition the mixture was stirred for 15 min letting the temperature slowly rise to ambient temperature. The reaction mixture was diluted with 10% aq. NaHSO3, stirred for 10 min and evaporated to ⅓ of the original volume. The residue was diluted with water and extracted twice with excess of ethyl acetate. The organics were dried, filtered and evaporated. The product was purified with flash chromatography. 4.087 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 5.97 (s, 2H), 7.42-7.52 (m, 1H).

1. additionwas added
2. temperaturemaintaining the internal temperature of the reaction mixture below 5° C
3. additionAfter addition the mixture
4. customslowly rise to ambient temperature
5. stirringstirred for 10 min
6. customevaporated
7. additionThe residue was diluted with water
8. extractionextracted twice with excess of ethyl acetate
9. customThe organics were dried
10. filtrationfiltered
11. customevaporated
12. customThe product was purified with flash chromatography

ORD record

ord-9b92c356888c47a985e4dbead1371678

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921378B2