Ethanol → Ethyl 3-fluoro-4-(trifluoromethoxy)benzoate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+].[CH2:25](O)[CH3:26]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:13])([F:14])[F:15])[C:5]([O:7][CH2:25][CH3:26])=[O:6]Participants
5
Procedure
To a solution of 3-fluoro-4-(trifluoromethoxy)benzoic acid (1.00 g, 4.46 mmol) in ethanol (10 ml) was added thionyl chloride (1.33 g, 11.2 mmol) at 0° C. The reaction solution was slowly warmed to room temperature, and stirred at the same temperature overnight. The reaction solution was poured into saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate twice. The organic layer was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→9:1) to give ethyl 3-fluoro-4-(trifluoromethoxy)benzoate (0.72 g, 64%) as a colorless and clear oil.
Workup
- extractionextracted with ethyl acetate twice
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→9:1)
Sources & evidence
- ORD record
- ord-691dfc1024ad4153a62788f5fe246dd1
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987445B2
Reaction notes
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