1,2-Dichloroethane → 1,1-Bis(4-dimethylaminophenyl)-2-bromopropene

Participants

Reaction Conditions

Reaction Steps

Into a reactor were introduced 13.6 g (48.5 mmol) of the 1,1-bis(4-dimethylaminophenyl)propene and 54 mL of 1,2-dichloroethane under a nitrogen atmosphere. The contents were cooled to 0° C. Thereto was gradually added dropwise 7.76 g (48.5 mmol) of bromine. The resultant mixture was stirred at room temperature for 2.5 hours. Thereafter, 15.7 mL (194 mmol) of pyridine and 109 mL of toluene were added thereto and this mixture was stirred at 80° C. for 3 hours. After being cooled, the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, subsequently dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrate was purified by column chromatography and then crystallized from methanol to obtain 12.0 g (69%) of the target compound as green-yellow crystals.

Provenance & Evidence