Methyl iodide → 1-Fluoro-2,3-dimethoxybenzene

HRID 525885

Reaktionsgleichung

Reaktionsgleichung von HRID 525885
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1O.[C:10](=[O:13])([O-])[O-].[K+].[K+].I[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:17])[C:3]=1[O:13][CH3:10]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 677643-Fluorocatechol

Produkt 1

HCID 27589791-Fluoro-2,3-dimethoxybenzeneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-fluorobenzene-1,2-diol (145 g, 1132 mmol), potassium carbonate (313 g, 2264 mmol) and iodomethane (177 mL, 2830 mmol) in N,N-Dimethylformamide (DMF) (300 mL) was stirred at RT for 48 h. LCMS showed the complete consuption of starting material. The mixture was diluted with ethyl acetate (EA), filtered, washed with water, dried and evaporated in vacuo. The crude material was purified by normal phase automatic silica gel column chromatography (Combiflash RF, 220 g column), eluting with EA/Hexane (10%-80%) to afford 1-fluoro-2,3-dimethoxybenzene (149 g, 954 mmol, 84% yield) as a colorless oil. LCMS (M+H)+: 157.0.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with water
  3. customdried
  4. customevaporated in vacuo
  5. customThe crude material was purified by normal phase automatic silica gel column chromatography (Combiflash RF, 220 g column)
  6. washeluting with EA/Hexane (10%-80%)

Quellen und Nachweise

ORD-Eintrag
ord-590ab0175ed64104a24f886df0608776
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340556B2

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