Dimethyl Sulfoxide → 2-Bromo-9,9-dibutyl-9H-fluorene

Participants

Reaction Steps

Under a nitrogen atmosphere, to a solution obtained by dissolving 20.8 parts of potassium tert-butoxide in 102 parts of dimethylsulfoxide (DMSO), a solution obtained by dissolving 15.4 parts of 2-bromofluorene in 153 parts of dimethylsulfoxide (DMSO) was added dropwise. After stirring for 30 minutes, while keeping the reaction solution temperature to 40 to 45° C., 27.8 parts of butyl iodide was added dropwise. After stirring at 40° C. for 40 minutes, the reaction solution was added to ice water. The reaction mixture was extracted with chloroform-water, the chloroform phase was dried over magnesium sulfate, and then chloroform was distilled off to obtain a brown tarry solid. This brown tarry solid was dissolved in a small amount of chloroform, and separated and purified by column chromatography (hexane) to obtain 12.6 parts of 2-bromo-9,9-dibutylfluorene as a colorless crystal.

Provenance & Evidence