Hydrogen Bromide → 6-chloro-2,3-dihydro-1H-inden-4-ol
Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[C:4]([O:11]C)[CH:3]=1.Br>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To 6-chloro-4-methoxyindane (12.0 g, 0.072 mol) was added hydrogen bromide (30 wt. % in acetic acid, 325 mL) and the reaction mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (750 mL), washed with water (3×500 mL), saturated aqueous sodium bicarbonate (2×500 m/L), saturated aqueous sodium chloride (500 mL), dried (sodium sulfate) and the solvent was removed in vacuo to provide a brown oil. Purification by flash column chromatography (silica, dichloromethane) provided 10.5 g (80%) of 6-chloroindan-4-ol as a pale yellow solid. mp 56-59° C.; Anal. calcd. for C9H9ClO.0.2H2O: C, 62.77; H, 5.50. Found: C, 62.75; H, 5.26.