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(b) 4-difluoromethoxy-3-methoxyacetophenone 20.8 g of 4-hydroxy-3-methoxyacetophenone are dissolved in 350 ml of dioxane and 350 ml of water by the addition of 30 g of sodium hydroxide, and the resulting solution is heated to 60. While stirring continuously, chlorodifluoromethane is passed into the solution until uptake of the gas stops (about 4 hours). The solution is cooled, and the resulting precipitate is filtered off with suction and washed three times with 40 ml of diethyl ether each time. The solution is diluted with water to twice its volume and likewise extracted three times with 100 ml of diethyl ether each time. The combined ether extracts are dried over magnesium sulfate and evaporated in vacuo; the residue is crystallized from petroleum ether (boiling point 50 to 70). 19 g (70.4% of theory) of 4-difluoromethoxy-3-methoxyacetophenone (M.P. 68) are obtained.
1,1-bis(ethylsulfanyl)-4-(4'-(difluoromethoxy)-3'-methoxyphenyl)-2-trifluoromethylbut-1-ene-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In this example, reference is made to the compound, having relatively to the structure of the general compound (I), R1=H, RF=CF3, R2=H, R3=4-(difluoromethoxy)-3-methoxy-phenyl. A solution of potassium hydride and a solution of 4-(difluoromethoxy)-3-methoxy-acetophenone is mixed preferably under an argon atmosphere at 0 C., in the presence of a solvent, preferably tetrahydrofurane (THF), this forms the mixture 1. To said mixture 1, after 10 to 20 mins of stirring, preferably 15 mins, is added a solution of perfluoroketene dithioacetal of formula (III′), this forms the mixture 2. Said mixture 2 is stirred at room temperature for 2 h 45 to 3 h 30, preferably 3 h. The current reaction occurring within the mixture 2 is hydrolyzed with water. The aqueous phase of the mixture 2, is notably extracted with ether. The organic phase of the mixture 2 is preferably dried on magnesium sulphate. The organic phase of the mixture 2 is filtered and evaporated preferably under reduced pressure. A chromatography on a column is carried out in order to obtain, advantageously as an oil, the compound (V″″′) of formula C17H19F5O3S2 called 1,1-Bis(ethylsulfanyl)-4-(4′-(difluoromethoxy)-3′-m ethoxy-phenyl)-2-trifluoromethyl-but-1-ene-4-one and preferably a silica column is used.
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