Sulfuric Acid → (4-Fluoro-3-iodophenyl)methanol
Reaktionsgleichung
N[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:20].[K+]>O>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][OH:6])=[CH:3][C:2]=1[I:20]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
The product from example 30A (7.0 g, 50 mmol) in water (100 mL) at 0° C. was treated slowly with concentrated sulfuric acid (30 mL) at a rate to maintain the temperature below 10° C. and then treated dropwise with an aqueous solution of sodium nitrite (3.45 g, 50 mmol). This solution was then added to a solution of potassium iodide (8.13 g, 50 mmol) in water (15 mL), heated to 60° C. for 2 hours, cooled and extracted with methylene chloride. The methylene chloride layer was washed with 10% sodium hydroxide, washed with 1 M sodium thiosulfate, washed with 10% hydrochloric acid, washed with aqueous sodium bicarbonate, dried (sodium sulfate), filtered, and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3) to provide 6.4 g of the title compound.
Aufarbeitung
- temperatureto maintain the temperature below 10° C.
- temperaturecooled
- extractionextracted with methylene chloride
- washThe methylene chloride layer was washed with 10% sodium hydroxide
- washwashed with 1 M sodium thiosulfate
- washwashed with 10% hydrochloric acid
- washwashed with aqueous sodium bicarbonate
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)
Quellen und Nachweise
- ORD-Eintrag
- ord-27b200abba034e8786ee7fdfed2be999
- Quelldatensatz
- uspto-grants-2001_02
- Patentnummer
- US06191140B1
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