Hydrochloric Acid → HCID 58113574, compound

Participants

Reaction Steps

5.36 g (7.52 mmol) of 9,9-di(4-methoxyphenyl)-2,7-bis(diphenylamino)fluorene (Compound 2) is dissolved in 25 ml of dichloromethane and the solution cooled in a dry ice-acetone bath under the protection of flowing nitrogen. To this solution, 34 ml (34 mmol) of a 1.0 M solution of boron tribromide in dichloromethane is added dropwise while the reaction is stirred. After the addition of boron tribromide, the reaction mixture is allowed to warm to room temperature and is stirred at room temperature overnight. The reaction mixture is then poured into 300 g of crushed ice. Concentrated HCl (1.0 ml) is added and the aqueous mixture stirred at room temperature for 2 h. The mixture is then extracted with dichloromethane and the combined organic layer is dried over anhydrous magnesium sulfate. The solution is filtered and the solvent removed on a rotary evaporator. The crude product is re-dissolved in a small amount of ethyl acetate and purified on a silica gel column eluted by a mixture of ethyl acetate and hexane (9:1 v/v). After the solvent is removed, the solid is re-crystallized from the mixed solvent of ethanol and ethyl acetate to give 3.5 g of the final product as off-white crystals. Purity: 96.7 percent (HPLC)

Provenance & Evidence