Chlorosulfonic acid → 5-Chlorosulphonyl-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole
Reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][C:4]1([C:13]([F:16])([F:15])[F:14])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5]1.[Cl:19][S:20](O)(=[O:22])=[O:21]>C(Cl)(Cl)Cl>[Cl:19][S:20]([C:11]1[CH:10]=[CH:9][C:7]2[O:8][C:4]([CH2:3][C:2]([F:1])([F:17])[F:18])([C:13]([F:15])([F:14])[F:16])[O:5][C:6]=2[CH:12]=1)(=[O:22])=[O:21]Participants
4
Procedure
136 g of 2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole were dissolved in 125 ml of chloroform. 175 g of chlorosulphonic acid were added dropwise at 0° C., while stirring, and the mixture was subsequently stirred at room temperature until the evolution of gas had ended. It was then poured onto 750 g of ice-water, the phases were separated and the aqueous phase was extracted with chloroform. The combined organic phases were washed with ice-water and sodium bicarbonate solution, dried with magnesium sulphate and freed from readily volatile constituents on a rotary evaporator. 133 g of product were obtained (=72% of theory), and the melting point was 55° to 57° C. 19F-NMR: -60.8 and -86.5 ppm. 1H-NMR: 3.13 ppm.
Workup
- stirringthe mixture was subsequently stirred at room temperature until the evolution of gas
- customthe phases were separated
- extractionthe aqueous phase was extracted with chloroform
- washThe combined organic phases were washed with ice-water and sodium bicarbonate solution
- dry with materialdried with magnesium sulphate
- customfreed from readily volatile constituents on a rotary evaporator
Sources & evidence
- ORD record
- ord-e022dfe11d9a42fda923bf760f7b5aaf
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05482956
Reaction notes
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