Bromine → HCID 22995025, compound
Reaction equation
[CH3:1][C:2]12[CH2:13][CH2:12][C:9]([CH3:14])([CH2:10][CH2:11]1)[C:8]1[CH:7]=[CH:6][C:5]([OH:15])=[CH:4][C:3]2=1.[Br:16]Br>C(O)(=O)C>[Br:16][C:6]1[C:5]([OH:15])=[CH:4][C:3]2[C:2]3([CH3:1])[CH2:13][CH2:12][C:9]([CH3:14])([C:8]=2[CH:7]=1)[CH2:10][CH2:11]3Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 1,8-dimethyltricyclo[6.2.2.02,7]dodeca-2(7),3,5-trien-4-ol (Compound 2, 1.58 g, 7.81 mmol) in 10 mL of glacial acetic acid was added bromine (0.40 mL, 7.81 mmol). The reaction mixture was stirred at 25° C. for 4 hours then quenched with 10% Na2S2O3 and extracted with Et2O. The combined ether extracts were washed with water and brine, and dried over Na2SO4, and filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate:hexane (2:98) to yield the title compound as a yellow oil.