Sulfuric Acid → HCID 18989454, compound

Participants

Reaction Conditions

Reaction Steps

121.1 ml (0.194 mol) of a 1.6M solution of n-butyllithium in hexane are added dropwise to a solution, cooled to -10° C., of 21.5 g (0.212 mol) of diisopropylamine in 194 ml of anhydrous THF. The mixture is stirred for 10 min at -10° C. under a nitrogen atmosphere, is then cooled to -76° C. and a solution of 37.4 g (0.194 mol) of 1-bromo-2,4-difluorobenzene in 270 ml of anhydrous THF is added dropwise over 30 minutes, at a temperature below -70° C. The mixture is stirred for 2 minutes at -70° C. and then a solution of 14.7 g (0.212 mol) of acrolein in 30 ml of anhydrous THF is added dropwise over 10 minutes at a temperature below -60° C. The mixture is then stirred for 30 minutes at -70° C., and the temperature is then allowed to return to 0° C. The mixture is poured onto a mixture of 350 g of ice and 35 ml of concentrated H2SO4. Extraction with ether, washing with water, drying over Na2SO4, filtration, evaporation under vacuum and distillation are carried out. Weight obtained: 29 g (Yd.=60%) B.p.0.5 =86°-88° C.

Provenance & Evidence