Hydrogen Bromide → 7,9a-Dibromo-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

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Reaction Steps

4.50 Grams of 8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone was dissolved in 50 ml of acetic acid and to the solution were gradually added dropwise 0.2 ml of hydrobromic acid and 1.3 ml of bromine, followed by refluxing under heating for 1 hour. The reaction mixture was poured into ice water and extracted with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in this order and then dried with magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10) and then recyrstallized from ethanol to obtain 3.86 g of 7,9a-dibromo-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone.

Provenance & Evidence