Hydrogen Bromide → Ethyl 4-benzyl-3-bromobutyrate

HRID 1291902Notes

Reaction equation

HRID 1291902 reaction equation
[CH2:1]([CH:8]1CO[C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:14].O.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].[CH2:22](O)[CH3:23]>>[CH2:1]([CH2:8][CH:9]([Br:14])[CH2:10][C:16]([O:17][CH2:22][CH3:23])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 5150640Dihydro-4-(phenylmethyl)-2(3H)-furanone

Product 1

HCID 18918606Ethyl 4-benzyl-3-bromobutyrate

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)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe organic layer filterd through phase separating paper
  3. customevaporated

Sources & evidence

ORD record
ord-e578e4b44e7e4aec860b17957be2959f
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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