Dimethyl Sulfoxide → HCID 89544754, Verbindung

HRID 2283389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283389
Br[CH2:2][C:3]1[C:4]([F:18])=[C:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[C:6]([Cl:9])=[CH:7][CH:8]=1.C(=O)(O)[O-:20].[Na+].CS(C)=O>C(OCC)(=O)C>[C:10]([C:5]1[C:4]([F:18])=[C:3]([CH:8]=[CH:7][C:6]=1[Cl:9])[CH:2]=[O:20])(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 89544688HCID 89544688, Verbindung

Produkt 1

HCID 89544754HCID 89544754, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Step 3 A mixture of (3-bromomethyl-6-chloro-2-fluoro-phenyl)-phenyl-methanone (292 mg, 0.896 mmol), sodium bicarbonate (700 mg, 8.33 mmol) and dimethylsulfoxide (10 ml) was heated to 80 degC for 3 hours. The reaction mixture was then allowed to cool, ethyl acetate was added, and the mixture was washed with water, aqueous lithium chloride and brine before drying (MgSO4) and concentrating in vacuo. The residue was purified by silica chromatography eluting with 0-20% ethyl acetate/petroleum ether to furnish 3-benzoyl-4-chloro-2-fluoro-benzaldehyde (115 mg oil, 90% clean). 1H NMR (400 MHz, CDCl3): 10.34 (1H, s), 7.97 (1H, dd), 7.91-7.86 (2H, m), 7.72-7.67 (1H, m), 7.55 (2H, t), 7.44 (1H, d), 7.28 (1H, s). MS: [M+NH4]+ 280

Aufarbeitung

  1. temperaturewas heated to 80 degC for 3 hours
  2. temperatureto cool
  3. washthe mixture was washed with water, aqueous lithium chloride and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating in vacuo
  6. customThe residue was purified by silica chromatography
  7. washeluting with 0-20% ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-4eb91cc340e64dcc933917224e2eece9
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145354B2

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