Carbon Dioxide → 3-(Chloromethoxy)-1,1,1,2,2-pentafluoropropane

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Reaction Conditions

Reaction Steps

Methyl 2,2,3,3,3-pentafluoropropyl ether (225g, 1.37 mole) in a flask fitted with a dry ice cooled condensor and moisture trap was stirred, heated to 33°C, irradiated with ultraviolet light, and sulfuryl chloride (174 g, 1.29 mole) was added dropwise. The reaction temperature dropped to about 0°C as SO2 returned from the condensor. The condensor was allowed to warm gradually to permit SO2 to escape and the reaction temperature to rise to about 33°C to complete the chlorination. The product was washed with ice cold water then with dilute sodium hydroxide solution to remove SO2 and dried to give 250 g of crude XXVII. This was fractionally distilled to give XXVII, b760 87.1-88.5; yield 159 g, purity 92% by GLC. The structure of XXVII was confirmed by proton NMR spectroscopy.

Provenance & Evidence