2-Bromoethanol → 2,2'-(2,7-Dibromo-9H-fluorene-9,9-diyl)di(ethan-1-ol)

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Reaction Conditions

Reaction Steps

A mixture containing 5.0 grams of 2,7-dibromofluorene, 3.1 grams of sodium hydroxide and 0.35 grams of Benzyltriethylammonium chloride in 50 ml of dimethylsulfoxide was stirred and to it was added 9.7 grams of the tetrahydropyranyl ether of 2-bromoethanol. The temperature rose slowly to 50° C. The temperature was maintained at 35° C. for 1 hr after which the mixture was added to 100 ml of water and 50 ml of ethyl acetate and 50 ml hexane. The organic layer was removed washed 2× with 100 ml of water and dried over sodium sulfate. The solvent was removed and 150 ml of ethanol added followed by 0.5 grams p-toluene sulfonic acid. The mixture was stirred at 70° C. for 30 min. The mixture was cooled and treated with aqueous potassium carbonate to ˜pH8. The solvent was removed and the residue treated with 50 ml of 1;1 ethyl acetate:hexane and 25 ml of water the solid was filtered and washed with water. Recrystallization from 1:1 ethyl acetate hexane to give 4.5 grams of 2-[2,7-dibromo-9-(2-hydroxy-ethyl)-9H-fluoren-9-yl]-ethanol which was esterified by the process described in example 1 to give 3.8 grams of Acrylic acid 2-[9-(2-acryloyloxy-ethyl)-2,7-dibromo-9H-fluoren-9-yl]-ethyl ester(4). This product was verified by NMR analysis to be present and pure.

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