1,4-Dioxane → 1-Bromo-5-isocyanatopentane

Participants

Reaction Conditions

Reaction Steps

To a solution of trimethylsilylazide (7.46 mL, 93.67 mmol) in dioxane (10 mL), 6-bromohexanoyl chloride (10 g, 46.83 mmol) was added and the solution was heated at 80° C. for 4 hours. The reaction mixture was concentrated to give a liquid. Distillation (oil bath temp. 135° C., distilling temperature 94° C.) of the liquid yielded 7 g (78%) of the product as a liquid: 1H-NMR (CDCl3) δ1.50-1.92 (m, 6 H), 3.33 (t, J=7.0 Hz, 2H), 3.43 (t, J=7.0 Hz, 2H). IR: 2360 cm-1.

Provenance & Evidence