Thionyl Chloride → 5-(Chloromethyl)-2-(trifluoromethyl)pyridine

HRID 512135

Reaktionsgleichung

Reaktionsgleichung von HRID 512135
S(Cl)([Cl:3])=O.[F:5][C:6]([F:16])([F:15])[C:7]1[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([F:16])([F:15])[F:5])=[N:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 36138956-(Trifluoromethyl)pyridine-3-methanol

Produkt 1

HCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Thionyl chloride (40.3 mL, 554 mmol) was slowly added to a solution of (6-trifluoromethylpyridin-3-yl)-methanol (19.6 g, 111 mmol) in DCM (195 mL) at room temperature under nitrogen. The reaction mixture was stirred at reflux for 16 hours then concentrated under reduced pressure. The residue was dissolved in AcOEt (200 mL), washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude 5-chloromethyl-2-trifluoromethylpyridine as a brown oil which was used in the following step without further purification (19.5 g, 90%). 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (s, 1 H), 7.94 (d, J=8.4 Hz, 1 H), 7.72 (d, J=8.4 Hz 1H), 4.66 (s, 2 H). 19F NMR (400 MHz, CDCl3) δ 168 cm−1. MS m/z 196.15; 198.09

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. concentrationthen concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in AcOEt (200 mL)
  4. washwashed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-71b55fac469c45f183426faa2cebeaec
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102591B2

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