Methyl iodide → 1-Bromo-5-fluoro-4-methoxy-2-methylbenzene

HRID 529414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529414
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([O:9][CH3:11])=[CH:6][C:7]=1[CH3:8]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 108997434-Bromo-2-fluoro-5-methylphenol

Produkt 1

HCID 227282131-Bromo-5-fluoro-4-methoxy-2-methylbenzeneAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Bromo-2-fluoro-5-methylphenol (40 g, 0.19 mol), cesium carbonate (75 g, 0.23 mol), and iodomethane (15 ml, 0.23 mol) were combined in 100 ml of DMF and stirred at RT for one hour (exothermic). The solution was diluted with ethyl acetate and filtered. The solution was washed with water twice, dried with anhydrous sodium sulfate, filtered, and concentrated. The product was purified via silica gel column chromatography (RediSep 330 g column) using 0-50% ethyl acetate in hexane to afford 1-bromo-5-fluoro-4-methoxy-2-methylbenzene (38 g, 89% yield) as a colorless liquid. No [M+H] peak by LCMS. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.24 (s, 3 H) 3.76 (s, 3 H) 6.73 (d, J=8.80 Hz, 1 H) 7.13 (d, J=10.56 Hz, 1 H)

Aufarbeitung

  1. filtrationfiltered
  2. washThe solution was washed with water twice
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified via silica gel column chromatography (RediSep 330 g column)

Quellen und Nachweise

ORD-Eintrag
ord-fcffb780bad24fd6b9522ba514240085
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346827B2

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