Thionyl Chloride → 2-(3-(Chloromethyl)phenoxy)-6-methylpyridine

HRID 1666389

Reaktionsgleichung

Reaktionsgleichung von HRID 1666389
[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH2:15]O)[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:19][CH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 668761143-[(6-Methyl-2-pyridinyl)oxy]benzenemethanol

Produkt 1

HCID 668758892-(3-(Chloromethyl)phenoxy)-6-methylpyridineAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(3-(6-Methylpyridin-2-yloxy)phenyl)methanol from Step 1 (3.7 g, 17 mmol), in dichloromethane (50 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (1.50 mL, 20.6 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 3 h. Saturated aqueous sodium bicarbonate (20 mL) was added and the mixture was stirred at RT for 5 min. The organic layer was separated, dried over sodium sulfate, filtered and concentrated by evaporation to afford the title compound (4.0 g, 99% yield) as an oil.

Aufarbeitung

  1. stirringthe mixture was stirred at RT for 5 min
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-ee0ee0118cc04bb4a36149663ad37520
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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