Methanol → (OC-6-21)-[3-Bromo-5-(methoxycarbonyl)phenyl]pentafluorosulfur
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:21]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:10]=1)[C:5]([O:7][CH3:21])=[O:6]Participants
Procedure
5.0 g (15.3 mmol) of the compound of Example 15A were dissolved in 150 ml of methanol and 2.2 ml (30.6 mmol) of thionyl chloride were added dropwise at RT. The reaction mixture was then heated under reflux for 4 h. After cooling to RT, the major part of the solvent except for a residual volume of about 50 ml was removed on a rotary evaporator. The residue was diluted with ethyl acetate and washed successively with water, saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying over magnesium sulphate, the mixture was filtered and concentrated. The crude product obtained in this manner was purified by filtration with suction over about 50 g of silica gel with dichloromethane as mobile phase. Re-concentration gave 5.06 g (97% of theory) of the title compound.
Workup
- temperatureThe reaction mixture was then heated
- temperatureunder reflux for 4 h
- customthe major part of the solvent except for a residual volume of about 50 ml was removed on a rotary evaporator
- additionThe residue was diluted with ethyl acetate
- washwashed successively with water, saturated sodium bicarbonate solution and saturated sodium chloride solution
- dry with materialAfter drying over magnesium sulphate
- filtrationthe mixture was filtered
- concentrationconcentrated
- customThe crude product obtained in this manner
- filtrationwas purified by filtration with suction over about 50 g of silica gel with dichloromethane as mobile phase
Sources & evidence
- ORD record
- ord-4938a22864b24491a312bd862e4ba6f0
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394309B2
Reaction notes
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