Benzyl Bromide → HCID 18782009, compound

Participants

Reaction Steps

A solution of 4-methylthioazetidin-2-one (1.0 g, 8.53 mmol) in dry THF (10 ml) was added dropwise to a suspension of NaH (0.35 g, 8.63 mmol) in dry THF (5 ml) at -20° C. under an inert atmosphere. Benzyl bromide (1.46 g, 8.53 mmol) in dry THF (10 ml) was added dropwise over 15 minutes at -55° C. The resultant mixture was stirred for 2 hours at room temperature, poured onto ice/water (50 g) and filtered, washed with brine and water, dried (MgSO4), and evaporated under reduced pressure to a yellow oil (1.62 g). This was purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate to give a yellow solid (0.98 g, 55%), m.p. 26-28° C.

Provenance & Evidence