Reaction #2347

Reaction equation

sodium carbonate

hydrogen bromide

3-benzylbutyrolactone

ethanol

water

→

ethyl 4-benzyl-3-bromobutyrate

Conditions

Workup

1. 1
   ExtractionThe mixture was extracted with ethyl acetate
2. 2
   Otherthe organic layer filterd through phase separating paper
3. 3
   Otherevaporated

Procedure

A solution of RS 3-benzylbutyrolactone (1.14 g) in ethanol (20 ml) was stirred at 5° C. and gassed for 4 hours with a slow stream of hydrogen bromide. The solution was kept at 5° C. for 20 hours and water (70 ml) added followed by sodium carbonate to neutralise the acid. The mixture was extracted with ethyl acetate and the organic layer filterd through phase separating paper and evaporated to give ethyl 4-benzyl-3-bromobutyrate as an oil; NMR(CDCl3) δ 7.24(5H,m), 4.13(2H,q); 3.45(2H,m), 2.62(2H,d), 2.44(3H,m), 1.25(3H,t); m/e 285(M+H)+.

Source