Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[CH3:13].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:12][CH3:13])=[O:5]Participants
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2.5 g (27.0 mmol) of 2-fluoro-4-iodobenzoic acid (Compound B) in 11 mL (8.6 g, 187.5 mmol) of ethanol was added 0.3 mL of c. sulfuric acid. The reaction mixture was heated to reflux in an oil bath (90° C.) for 1.75 hours, fitted with a short path distillation apparatus, distilled and then allowed to cool to ambient temperature. The reaction mixture was extracted and partitioned between pentane and water and the layers were separated. The aqueous phase was washed with pentane and the organic phases were combined. The combined organic phase was washed sequentially with sat. NaHCO3 (aq.) solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo to a purple oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as an orange oil.
Workup
- temperatureThe reaction mixture was heated
- customfitted with a short path distillation apparatus
- distillationdistilled
- temperatureto cool to ambient temperature
- extractionThe reaction mixture was extracted
- custompartitioned between pentane and water
- customthe layers were separated
- washThe aqueous phase was washed with pentane
- washThe combined organic phase was washed sequentially with sat. NaHCO3 (aq.) solution, water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo to a purple oil
- customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-64d682d8bd5a4b6aaf6e605f6e60de64
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455701B1
Linked notes
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