Dimethylformamide → 4-(2-Propen-1-yloxy)-9H-carbazole

Participants

Reaction Steps

138 g of potassium carbonate was added to N,N-dimethylformamide (500 mL) solution of 121.9 g of 4-hydroxycarbazole. Under stirring, 88.6 g of allyl bromide was added thereto and the reaction mixture was stirred at 80° C. for 5 hours. The reaction mixture was allowed to cool, 3.5 L of water was added thereto, and extracted twice with 1 L of ethyl acetate. The combined organic layer was washed with 1 L of brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo. The residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:1), and 129 g of the subject compound was prepared.

Provenance & Evidence