Dimethyl Sulfoxide → Difluoro-phenyl-acetaldehyde

HRID 1881119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881119
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][OH:14].C(N(CC)CC)C>C(Cl)Cl.O>[F:11][C:12]([F:21])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:13]=[O:14]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 97938912,2-Difluoro-2-phenylethanol

Produkt 1

HCID 14644933Difluoro-phenyl-acetaldehydeAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of oxalyl chloride (2.66 g, 21.0 mmol) in DCM (300 mL) was added DMSO (2.5 mL, 35.0 mmol) at 60° C. The mixture was stirred for 30 min. Then 2,2-difluoro-2-phenyl-ethanol (28.1 g, 18.0 mmol) was added at the same temperature. The mixture was stirred for another 30 min. Triethylamine (11.1 mL, 80.0 mmol) was added and then the mixture was stirred for 2 h at room temperature. Water was added and the organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product difluoro-phenyl-acetaldehyde (828 mg, 30%), which was used to the next step without further purification.

Aufarbeitung

  1. stirringThe mixture was stirred for another 30 min
  2. stirringthe mixture was stirred for 2 h at room temperature
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8c84a1a33d1943b998c0e9b40060c697
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318778B2

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