N-bromobutanimide → HCID 11539960, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 ml round bottom flask with addition funnel was added 30 ml of methylene chloride and 0.38 g (1 mmol) of the product from Example 19. The flask was cooled to −78° C. and a solution of 0.18 g (1 mmol) of N-bromosuccinimide in 10 ml of methylene chloride was slowly added via addition funnel. After addition was complete, the reaction was allowed to stir at this temperature for 1 hr, then cooling removed. When the reaction had warmed to room temperature it was extracted with 20 ml of saturated sodium bicarbonate solution and separated. The aqueous layer was extracted twice with 10 ml of methylene chloride and the combined organic layers were dried (MgSO4) and concentrated. The crude solid was subjected to column chromatography eluting with 40% ethyl acetate:hexane to yield 0.32 g (69%) of solid which was crystallized from ethyl acetate:hexane to produce colorless crystals, mp 119° C. (dec).

Provenance & Evidence