Hydrochloric Acid → 7-bromo-9h-fluoren-2-ol

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([O:15]C(=O)C)=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-].[Li+].Cl>C(O)CO>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

Procedure

A mixture of 2-bromo-7-acetoxyfluorene (69 g), lithium hydroxide (9 g) and ethylene glycol (350 mL) was heated for one hour while refluxing. The reaction mixture was poured into 6M-hydrochloric acid (300 mL) to terminate the reaction, and the product was extracted with ethyl acetate (350 mL). The ethyl acetate layer was washed with a saturated sodium carbonate aqueous solution and dried on anhydrous magnesium sulfate. A residue obtained by distilling the solvent off under reduced pressure was recrystallized from chloroform to obtain 2-bromo-7-hydroxyfluorene (40 g) of colorless needle crystal. The melting point was 183-184° C.