Allyl bromide → 9-(Prop-2-en-1-yl)-9H-fluorene-9-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.50 mol/l, n-hexane solution) was slowly added dropwise to a solution of fluorene-9-carboxylic acid (3.0 g) in THF in an argon atmosphere at −78° C. The mixture was stirred at −78° C. for 30 min and then at 0° C. for 30 min. The stirred mixture was again cooled to −78° C. Allyl bromide (2.5 ml) was slowly added dropwise thereto at −78° C., and the mixture was stirred at −78° C. for 30 min and then at room temperature overnight. After the disappearance of fluorene-9-carboxylic acid was confirmed by TLC, a saturated aqueous ammonium chloride solution was slowly added to the reaction solution. Ethyl acetate was then added thereto to perform extraction. The organic layer was washed with a saturated aqueous sodium chloride solution and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to give 9-allyl-9H-fluorene-9-carboxylic acid (3.58 g) as a white solid.

Provenance & Evidence