Reaktionsgleichung
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].C([Li])CCC.[CH3:16][C:17]([CH3:19])=[O:18]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([C:17]([OH:18])([CH3:19])[CH3:16])[CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a stirred solution of 2-bromo-4-fluoro anisole (4.1 g, 20 mmol) in anhydrous THF (40 mL) cooled to −78° C. and maintained under an atmosphere of argon was added n-butyl lithium (8.8 mL of 2.5 M solution in hexanes, 22 mmol). After stirring at −78° C. for 45 minutes, the reaction mixture was treated with anhydrous acetone (5 mL). After 15 minutes, the reaction mixture was quenched with a saturated solution of ammonium chloride and extracted with three 50 mL portions of methylene chloride. Combined extracts were washed with three 25 mL portions of water, dried over anhydrous sodium sulfate, and the solvent was evaporated to give 2-(5-fluoro-2-methoxyphenyl)propan-2-ol as a light brown thick oil (85% yield) which solidified on standing. The crude product was used for the next reaction without further purification.
Aufarbeitung
- temperaturemaintained under an atmosphere of argon
- waitAfter 15 minutes
- customthe reaction mixture was quenched with a saturated solution of ammonium chloride
- extractionextracted with three 50 mL portions of methylene chloride
- washCombined extracts were washed with three 25 mL portions of water
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-f5210dcb51a346028c940970d24e133b
- Quelldatensatz
- uspto-grants-2007_03
- Patentnummer
- US07189758B2
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