Antimony trifluoride → Methyl 3-methoxy-4-(trifluoromethoxy)benzoate
Reaction equation
Br[C:2]([F:17])([F:16])[O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15].[Sb](F)(F)[F:19]>C(OCC)C.[Sb](Cl)(Cl)(Cl)(Cl)Cl>[CH3:15][O:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[O:3][C:2]([F:17])([F:19])[F:16])[C:8]([O:10][CH3:11])=[O:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 170 °C
Procedure
Antimony (V) Chloride (26.4 mg, 0.088 mmol) was added to a stirred, room temperature mixture of 173A (550 mg, 1.768 mmol) and antimony trifluoride (221 mg, 1.238 mmol) in a sealed tube, and the mixture was stirred at 170° C. for 4 h. The mixture was cooled, diluted with diethyl ether (50 mL), washed with water (50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel; 24 g prepacked column, eluting with EtOAc/isohexane=10% to give methyl 3-methoxy-4-(trifluoromethoxy)benzoate 173B (240 mg, 0.959 mmol, 54.3% yield) as a white solid.
Workup
- temperatureThe mixture was cooled
- washwashed with water (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
- wash24 g prepacked column, eluting with EtOAc/isohexane=10%
Sources & evidence
- ORD record
- ord-f55a0f17afa441148add2cc58971724b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592383B2
Reaction notes
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