Hydrochloric Acid → 1-(3-Dimethylamino-5-pentafluorosulfanylphenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

3-Dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide (980 mg) was dissolved in abs. THF (50 ml), and methylmagnesium bromide solution (2.1 ml; 3M solution in diethyl ether) was added dropwise while stirring at 0° C. After the addition had ended, the ice bath was removed and the mixture was stirred at RT for 1 h. To complete the reaction, more methylmagnesium bromide solution (0.3 ml) was added and the mixture was stirred for a further 2 h. After storing overnight in a refrigerator, the reaction mixture was admixed with 1 N hydrochloric acid while cooling. Addition of water and ethyl acetate was followed by extraction twice more with ethyl acetate, and the combined organic phases were dried with magnesium sulfate, filtered and concentrated. The residue was purified by means of chromatography on silica gel (100/0 to 50/50 n-heptane/ethyl acetate within 30 min). The product-containing fractions were combined, the solvent was removed and the residue was dried under high vacuum. 650 mg of the title compound were obtained.

Provenance & Evidence