Carbon tetrabromide → 4-(2-Bromoethyl)morpholine

Participants

Reaction Steps

To a mixture of 0.656 g (5 mmole) of 2-morpholin-4-yl-ethanol and 20 mL of dichloromethane at 0 degrees was added 2.49 g (7.5 mmole) of carbon tetrabromide and then 1.57 g (6 mmole) of triphenylphosphine. The mixture was stirred at ambient temperature overnight. The mixture was concentrated under reduced pressure and 50 mL of hexanes was added. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with ethyl acetate-hexanes (gradient 0:100-30:70) gave 0.580 g of 4-(2-bromo-ethyl)-morpholine as a colorless oil.

Provenance & Evidence