Carbon tetrabromide → Ethyl (+/-)-4-(4-bromomethyl-1,3-oxazol-2-yl)-3-phenylbutanoate

Participants

Reaction Steps

To a solution of ethyl (±)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoate (1.3 g, 4.49 mmole) in dry THF (20 mL) was added PPh3 (1.41 g, 5.39 mmole) then CBr4 (1.79 g, 5.39 mmole) at 0° C. After 20 min, the mixture was warmed to RT. After 2 hr, the mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel (20% EtOAc/hexanes) to give the title compound (1.38 g, 87%) as a colorless oil: MS (ES) m/e 352 (M+H)+.

Provenance & Evidence