Beta-Propiolactone → 3-(2-Bromo-3-formylphenoxy)propanoic acid

HRID 561837Notes

Reaction equation

HRID 561837 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC(C)([O-])C.[K+].[O:17]1[CH2:20][CH2:19][C:18]1=[O:21]>C1COCC1>[Br:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:20][CH2:19][C:18]([OH:21])=[O:17]

Participants

5

Reactant 3

HCID 2365Beta-PropiolactoneHCID 37146742-Bromo-3-hydroxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 866359223-(2-Bromo-3-formylphenoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-3-hydroxybenzaldehyde (1 eq.) in THF (1.2 M) was added sequentially potassium tert-butoxide (1.0 M THF solution, 0.8 eq.) and oxetan-2one at RT. The resulting yellow suspension was stirred at RT for 16 h. The reaction mixture was quenched with 10% aq. HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with 10% aq. HCl
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-3c08bec7f5174473a104ee045e6356f4
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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