Methyl iodide → 1-Bromo-4-chloro-2-fluoro-3-methoxybenzene

HRID 495016

Reaktionsgleichung

Reaktionsgleichung von HRID 495016
[Br:1][C:2]1[C:3]([F:10])=[C:4]([OH:9])[C:5]([Cl:8])=[CH:6][CH:7]=1.CI.[C:13](=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([O:9][CH3:13])[C:3]=1[F:10]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666010023-Bromo-6-chloro-2-fluorophenol

Produkt 1

HCID 666003671-Bromo-4-chloro-2-fluoro-3-methoxybenzeneAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A heterogeneous mixture of 3-bromo-6-chloro-2-fluorophenol (14.4 g, 0.064 mol), methyl iodide (13.5 g, 0.096 mol) and potassium carbonate (8.8 g, 0.064 mol) in acetonitrile (100 mL) was heated under reflux for two hours. The mixture was cooled, diluted with water (100 mL) and extracted with diethyl ether (2×150 mL). The combined extracts were dried and concentrated. The dark oil was purified by chromatography (5% ethyl acetate in hexanes) to give 1-bromo-4-chloro-2-fluoro-3-methoxybenzene (14.8 g, 0.062 mol) 1H NMR (CDCl3): δ 7.20 (m, 1H), 7.10 (dd, 1H), 4.0 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with diethyl ether (2×150 mL)
  5. customThe combined extracts were dried
  6. concentrationconcentrated
  7. customThe dark oil was purified by chromatography (5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4bd1fd11c85f47bba1e23f442a4380fa
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538214B2

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