Ethanol → Ethyl 5-bromofuran-2-carboxylate
Reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:14](O)[CH3:15]>>[Br:1][C:2]1[O:6][C:5]([C:7]([O:9][CH2:14][CH3:15])=[O:8])=[CH:4][CH:3]=1Participants
4
Procedure
To a stirred suspension of 8.43 g (44.14 mmol) of 5-bromo-2-furoic acid in 100 ml absolute ethanol was added 4 ml of thionyl chloride. This mixture was stirred at reflux for 3 hours and at room temperature for 18 hours. The solvent was removed in vacuo, the residual oil treated with 100 ml water and extracted with 3×75 ml ether. The combined ether extracts were washed with saturated NaHCO3 and saturated NaCl solutions and dried (MgSO4). Solvent was removed in vacuo and the residue kugelrohr distilled (60° C.; 0.4 mm) to give the captioned compound as a colorless oil.
Workup
- customThe solvent was removed in vacuo
- additionthe residual oil treated with 100 ml water
- extractionextracted with 3×75 ml ether
- washThe combined ether extracts were washed with saturated NaHCO3 and saturated NaCl solutions
- dry with materialdried (MgSO4)
- customSolvent was removed in vacuo
- distillationthe residue kugelrohr distilled (60° C.; 0.4 mm)
Sources & evidence
- ORD record
- ord-6e9379d5bbe64be4b5753b6641dc14eb
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04923884
Reaction notes
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