Boron tribromide → 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol
Reaction equation
C[O:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]3[CH:12]([CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8]3)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH:15]1[C:14]2[CH2:13][CH:12]3[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 7-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene (1.95 g, 9.65 mmol) in CH2Cl2 (20 mL) was added BBr3 (1M in CH2Cl2, 24 mmol) dropwise at 0° C. This mixture was stirred at 0° C. for one hour. The reaction mixture was then quenched with MeOH (5 mL). Aqueous sodium hydrogen carbonate (10 mL) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/heptane) provided 1.48 g of 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol.
Workup
- customThe reaction mixture was then quenched with MeOH (5 mL)
- additionAqueous sodium hydrogen carbonate (10 mL) was added
- stirringThe reaction mixture was stirred at room temperature overnight
- extractionThe reaction mixture was extracted with CH2Cl2
- washThe organic phase was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4f2b34b4d6364c17a2c519c7d3a8a763
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642603B2
Reaction notes
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