Benzene → HCID 19841467, compound

Participants

Reaction Steps

Into a 300 milliliter round bottom reaction flask was charged 14.9 grams (51.4 mmol) of 3,5-dichloro-4-(2,4-difluorophenoxy) aniline, 7.2 grams (53.9 mmol) of N-chlorosuccinimide (NCS), and 100 milliliters of benzene. The reaction mixture was refluxed for 2 hours after which time additional NCS (350 milligrams, 2.6 mmol) was added. Reflux was then continued for an additional 1 hour. The mixture was allowed to cool, diluted with ethyl acetate (200 milliliters), washed with H2O, saturated NaHCO3 and brine; dried over Na2SO4 and concentrated under reduced pressure. The oily product obtained was purified by flash column chromatography (1:1 hexane toluene) to afford 4-(2,4-difluorophenoxy)-2,3,5-trichloroaniline (9.8 grams, 30.2 mmol, 59%) as a dark brown oil. The structure of this material was verified by its H'-NMR spectrum (CDCl3) 7.30-6.10 (m, 3H), 6.75 (s, 1H), 4.18 (br s, 2H).

Provenance & Evidence