Water → 9-(4-bromobutyl)-9H-fluorene-9-carboxylic acid

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Reaction Steps

89 ml (0.11 mol) of a 1.6 M butyllithium solution in hexane are added dropwise at 0° C. to a solution of 21 g (0.1 mol) of 9-fluorenecarboxylic acid in 700 ml tetrahydrofuran under nitrogen and stirred for one hour. Then, still at 0° C., 13.13 ml (0.11 mol) of dibromobutane are added and the solution is stirred for 30 hours at ambient temperature. After this time, 50 ml of water are added and the mixture is stirred for 30 minutes. The solution is evaporated down, combined with water and extracted with 250 ml of diethyl ether. The aqueous phase is acidified with 150 ml of 1N hydrochloric acid and extracted three times with 250 ml of dichloromethane. The combined organic phases are dried over sodium sulphate and the solvent is removed.

Provenance & Evidence