Dimethyl Sulfoxide → 3-(3,4-Dichlorophenyl)-3-methylbutan-2-one

HRID 1627336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627336
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([CH3:24])([CH3:23])[CH:20]([OH:22])[CH3:21])[CH:15]=[CH:16][C:17]=1[Cl:18].CCN(CC)CC>C(Cl)Cl.O>[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([CH3:24])([CH3:23])[C:20](=[O:22])[CH3:21])[CH:15]=[CH:16][C:17]=1[Cl:18]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 667400023-(3,4-Dichlorophenyl)-3-methylbutan-2-ol

Produkt 1

HCID 212584633-(3,4-Dichlorophenyl)-3-methylbutan-2-oneAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

DMSO (14.7 mL, 205 mmol) was added dropwise to a solution of oxalyl chloride (9.0 mL, 103 mmol) in CH2Cl2 (200 mL) at −78° C. The reaction mixture was stirred for 30 min and a solution of 3-(3,4-dichlorophenyl)-3-methylbutan-2-ol (12 g, 51.4 mmol) in CH2Cl2 (50 mL) was added by cannula over 15 min. After stirring 30 min, Et3N (43 mL, 308 mmol) was added, and the reaction mixture was allowed to warm to room temperature over 1 h. Water (200 mL) was added, and the organic layer was separated. The aqueous layer was further extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography to give 3-(3,4-dichlorophenyl)-3-methylbutan-2-one (10.7 g, 89%). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 1H), 7.37 (m, 1H), 7.08 (d, 1H), 1.95 (s, 3H), 1.59 (s, 6H).

Aufarbeitung

  1. stirringAfter stirring 30 min
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was further extracted with CH2Cl2 (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d368ea0f0fdb46258032f6fc49df01ca
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785488B2

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