Iodine → 5-Bromo-2-(7-bromo-9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acid methyl ester

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Reaction Conditions

Reaction Steps

40 g (66 mmol) 15 is dissolved in 300 ml dichloromethane. The solution is cooled to 0° C., 1 g iodine is added and the mixture is stirred for 30 min. Then a solution of 11 g bromine in dichloromethane is slowly added by a dropping funnel. The solution is heated to reflux until the reaction is completed The reaction mixture is allowed to warm up to room temperature and of a 200 ml saturated Na2S2O3 solution is added. The organic layer is separated and the aqueous layer is extracted with dichloromethane. The unified organic layers are washed twice with 100 ml water dried over sodium sulfate, filtrated and the solvent is removed under vacuum. The residue is recystallisated from butanole to result white solid (38 g 55.6 mmol, yield: 84%)

Provenance & Evidence