HCID 20461933, compound → 2,5-Bis(difluoromethoxy)benzene-1-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

While cooling at 0° C., 21 ml of a 40% solution of sodium hydrogen sulfite are added dropwise to a solution of 3.0 g of copper sulfate pentahydrate in 90 ml of 32% hydrochloric acid. To the resultant solution is then made the simultaneous dropwise addition of 21 ml of a 40% solution of sodium hydrogen sulfite and a diazonium salt solution which has been cooled to -10° C. and obtained by the dropwise addition, with cooling, of 6.9 g of sodium nitrite in 10 ml of water, to a suspension of 50 ml of water, 15 of 32% hydrochloric acid and 26.2 g of 2.5-bis(difluoromethoxy)aniline hydrochloride. During this addition the temperature of the reaction mixture rises to 25° C., accompanied by the simultaneous evolution of gas. The reaction mixture is stirred for 2 hours, whereupon a brown oil precipitates. The organic phase is separated and the aqueous phase is extracted with methylene chloride. The organic phases are combined and evaporated to dryness, affording, as crude product, 12.7 g of 2.5-bis(difluoromethoxy)-phenyl sulfonyl chloride in the form of a brown oil.

Provenance & Evidence