Methyl iodide → 4-(2,6-Dichloro-4-methoxymethyl-phenoxy)-anisole

HRID 1168091

Reaktionsgleichung

Reaktionsgleichung von HRID 1168091
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][OH:19])[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[H-].[Na+].[H][H].[CH3:24]I>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][O:19][CH3:24])[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222856543,5-Dichloro-4-(4-methoxyphenoxy)benzyl AlcoholHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 222856594-(2,6-Dichloro-4-methoxymethyl-phenoxy)-anisoleAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the title compound of Step A (400 mg, 1.34 mmol) in dry dimethylformamide (13 mL) at 0° C. under nitrogen was added NaH (60% dispersion in mineral oil, 134 mg, 3.3 mmol). After stirring for 30 minutes at 0° C. until hydrogen evolution ceased, methyl iodide (949 mg, 6.61 mmol) was added. The reaction mixture was warmed to room temperature and stirred for about 19 hours. The solution was poured into water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with 1M HCl (3×100 ml), brine (100 ml), dried, filtered, and concentrated. The crude product was purified by preparative TLC (30% hexane in dichloromethane) to afford the title compound (410 mg). NMR (400 MHz, CDCl3) δ7.36 (s, 2H), 6.75-6.83 (m, 4H), 4.40 (s, 2H), 3.75 (s, 3H), 3.43 (s, 3H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined extracts were washed with 1M HCl (3×100 ml), brine (100 ml)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative TLC (30% hexane in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-567f5fcc4362481db6593d829cf33380
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620830B2

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