Butyl vinyl ether → HCID 86704186, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6.15 g (15 mmol) of N-(3-bromo-2-fluorophenyl)-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide in 35 mL of ethylenglycol in a flask equipped with a rubber septum, through which nitrogen is fluxed by a needle, 37.5 mg (0.15 mmol) of palladium acetate, 129 mg (0.30 mmol) of DPPP, 5.4 mL (37.5 mmol) of TEA and 5.9 mL (45 mmol) of n-butylvinylether were added consecutively. The mixture was heated at 120° C. under stirring for 6 h and then diluted with DCM and washed with brine. The organic layer was dried over Na2SO4 and evaporated, giving N-[3-(1-butoxyethenyl)-2-fluorophenyl]-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide as a brown oil. The latter, without any further purification, was dissolved in 65 mL of 1,4-dioxane and 11 mL of 1N HCl were added to the resulting solution. After 1 h under stirring at r.t. the reaction was complete. The solvent was then removed, the residue re-dissolved with DCM and washed with aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4 and evaporated. After trituration with diethylether 4.82 g (86%) of the title compound were collected by filtration.

Provenance & Evidence