Thionyl Chloride → 1-(4-(chloromethyl)-3-fluorophenyl)-1H-pyrazole

HRID 629408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629408
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>C1COCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:17][CH2:13][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:7][C:2]=1[F:1]

Komponenten

6

Edukt 2

HCID 24386Thionyl ChlorideHCID 59028616(2-fluoro-4-(1H-pyrazol-1-yl)phenyl)methanol

Produkt 1

HCID 590285991-(4-(chloromethyl)-3-fluorophenyl)-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of (2-fluoro-4-(1H-pyrazol-1-yl)phenyl)methanol (0.71 g) in THF (15.0 mL) was added thionyl chloride (0.40 mL) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, saturated aqueous sodium bicarbonate was added thereto, and the mixture was partitioned. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.50 g).

Aufarbeitung

  1. temperaturecooling
  2. additionwas added
  3. customthe mixture was partitioned
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4d3dc858a8384f9bb1f0238fb4487f11
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315458B2

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