Bromine → 9a-(2-Bromoacetyl)-1,2,3,4,4a,9a-hexahydrofluoren-9-one
Reaction equation
[Br:1]Br.[C:3]([C:6]12[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]2=[O:19])(=[O:5])[CH3:4]>CO>[Br:1][CH2:4][C:3]([C:6]12[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]2=[O:19])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Bromine (1.2 ml) was added to a mixture of 9a-acetyl-1,2,3,4,4a,9a-hexahydrofluoren-9-one (5 g) in methanol (20 ml) at 20-30° C. The reaction mixture was stirred for 2 hours and quenched with NaHCO3 solution (0.8 g NaHCO3 and 24 ml water). The mixture was extracted with CH2Cl2 (3×30 ml) and the organic phase was washed with water (30 ml) and dried over Na2SO4. Evaporation gave 6.6 g of the crude product which was used without further purification for the next step.