Thionyl Chloride → 2-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrile

HRID 705860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705860
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][Cl:25])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 668256082-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(hydroxymethyl)benzonitrile

Produkt 1

HCID 677735002-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrileAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-(hydroxymethyl)benzonitrile (500 mg, 1.526 mmol) in DCM (30 mL), was added thionyl chloride (1.671 mL, 22.89 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, concentrated and purified via flash chromatography to afford the title compound (479 mg, 89% yield) as a white solid. LCMS: rt=3.45 min

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
  6. custompurified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-52858346b9324b8981a0665c25bcb0bd
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

Notizen zur Reaktion

Wird geladen…