N-bromobutanimide → HCID 86714618, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence