Thionyl Chloride → 5-(Chloromethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile

HRID 705871

Reaktionsgleichung

Reaktionsgleichung von HRID 705871
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9].S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 668256575-(Hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile

Produkt 1

HCID 677727715-(Chloromethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrileAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of 5-(hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile (269 mg, 0.999 mmol) in DCM (20 mL), was added thionyl chloride (0.7 mL, 9.59 mmol) dropwise. The mixture was stirred at room temperature for 2 h. After removing the solvent, the residue was dissolved in DCM, then washed with water twice, dried over Na2SO4, and concentrated in vacuo to afford the title compound (275 mg, 96% yield) as a light green solid. LCMS: rt=3.54 min, [M+H+]=313

Aufarbeitung

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ffc30bd80f734719b9bf24a6ab371634
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

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