Ethanol → HCID 59377674, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH3:19][CH2:20]O>>[CH2:19]([O:12][C:11](=[O:13])[CH2:10][C:3]1[CH:4]=[C:5]([OH:9])[C:6]([F:8])=[CH:7][C:2]=1[Br:1])[CH3:20]Participants
4
Procedure
To a solution of (2-bromo-4-fluoro-5-hydroxy-phenyl)-acetic acid (5.06 g) in EtOH (100 ml) was added sulfuric acid (0.2 ml) and the mixture was stirred at room temperature for 24 hours. The mixture was heated at 70° C. with stirring for an additional 24 h. The mixture was evaporated to dryness under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc/9:1) gave (2-bromo-4-fluoro-5-hydroxy-phenyl)-acetic acid ethyl ester (4.66 g) as a solid.
Workup
- temperatureThe mixture was heated at 70° C.
- stirringwith stirring for an additional 24 h