Methyl iodide → 1-Fluoro-2-iodo-4-methoxy-5-methylbenzene

HRID 1438166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438166
[F:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].IC.CCOC(C)=O.CCCCCC>CC(C)=O.C(OCC)C>[CH3:11][O:9][C:5]1[CH:6]=[C:7]([I:8])[C:2]([F:1])=[CH:3][C:4]=1[CH3:10]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 598379984-Fluoro-5-iodo-2-methylphenol

Produkt 1

HCID 210705041-Fluoro-2-iodo-4-methoxy-5-methylbenzeneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 122C (1 g, 4 mmol) in acetone (20 mL) was added K2CO3 (1.64 g) and iodomethane (0.75 mL). The mixture was stirred at rt for 3 h. After TLC (10% EtOAc/Hexane) indicated the reaction was complete, the mixture was diluted with diethyl ether, washed with water and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography to give 122D (0.75 g, 70% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.16 (s, 3H) 3.78 (s, 3H) 6.85 (d, J=8.79 Hz, 1H) 7.05 (d, J=5.27 Hz, 1H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fac16e442e4044d1b186ddf190ca166b
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622585B2

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