N-bromobutanimide → HCID 10594137, compound

Participants

Reaction Steps

N-bromosuccinimde (14 g) was added in one portion to a stirred solution of 8-t-butyldimethylsilyloxyquinaldine (15 g) in chloroform at -40° C. under an inert atmosphere. The reaction was warmed to room temperature and then heated to reflux for 6 h. Further N-bromosuccinimide (6 g) was added to the reaction at room temperature and stirring continued for 3 days. The reaction mixture was poured into 5% aqueous sodium metabisulphite solution (300 ml) and extracted with chloroform (3×300 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to afford the title compound as an orange oil (16.4 g).

Provenance & Evidence