Ethyl 2-bromopropionate → HCID 20141170, compound

HRID 543428Notes

Reaction equation

HRID 543428 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10]C(C)([O-])C.[K+].Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:5][C:23]1([CH3:10])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 811292-BromobenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 20141170HCID 20141170, compoundYield 69%

Procedure

A 50 g (0.27 mole) sample of 2-bromobenzaldehyde was added to 33.3 g of dry potassium t-butoxide under N2 at -78°. A 48.9 g (0.27 mole) sample of ethyl 2-bromopropionate was added slowly with stirring. The mixture was allowed to warm to room temperature and stir for 18 hr. The mixture was partitioned between ether and dilute HCl. The ether was washed with brine, dried (MgSO4) and the solvent evaporated in vacuo. The residue was distilled under vacuum to give 53.2 g (69% yield) of ethyl 3-(2-bromophenyl)-2-methyloxiraneacetate as an oil, bp 110°-120° C., 0.005 mm/Hg.

Workup

  1. stirringstir for 18 hr
  2. customThe mixture was partitioned between ether and dilute HCl
  3. washThe ether was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-1d6499957cc24e06924b586f166d4f76
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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