Thionyl Chloride → 5-(Chloromethyl)-2-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 705863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705863
[F: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:25][CH2:17][C:14]1[CH:15]=[CH:16][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:19]([F:22])([F:21])[F:20])[CH:4]=2)=[C:10]([CH:13]=1)[C:11]#[N:12]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 668254512-{[4-Fluoro-3-(trifluoromethyl)phenyl]oxy}-5-(hydroxymethyl)benzonitrile

Produkt 1

HCID 677745815-(Chloromethyl)-2-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}benzonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of 2-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}-5-(hydroxymethyl)benzonitrile (700 mg, 2.249 mmol) in DCM (40 mL), was added thionyl chloride (2.462 mL, 33.7 mmol) dropwise. The mixture was stirred at room temperature for 1.5 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 (665 mg, 90% yield) as a light yellow solid. LCMS: rt=3.71 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 in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-86c632156d344f0fb902590aefd0f09d
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

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