Water → 3-Chloro-2-[2-chloro-4-(methanesulfonyl)benzoyl]cyclohex-2-en-1-one

HRID 34510

Reaktionsgleichung

Reaktionsgleichung von HRID 34510
[Cl:1][C:2]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=O)=[O:5].C(Cl)(=O)C([Cl:25])=O.CN(C)C=O.O>C(Cl)Cl>[Cl:25][C:7]1[CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:6]=1[C:4](=[O:5])[C:3]1[CH:14]=[CH:15][C:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:17][C:2]=1[Cl:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 91760Sulcotrione

Produkt 1

HCID 142799823-Chloro-2-[2-chloro-4-(methanesulfonyl)benzoyl]cyclohex-2-en-1-oneAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(2-Chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione (9.8 g, 30 millimole) was dissolved in 100 ml methylene chloride and stirred at room temperature. To this solution was added oxalyl chloride (5.7 g, 45 mmol) followed by dimethylformamide (0.5 ml) in portions small enough to control effervescence. The resulting solution was stirred for 4 hours and then poured into water and extracted with methylene chloride. The organic layer was washed again with water, saturated K2CO3 solution and then dried with MgSO4 and the solvent evaporated to yield 3-chloro-2-(2chloro-4-methanesulfonylbenzoyl)cyclohex-2-enone (7.3 g, 70%) as an oil which was used without further purification.

Aufarbeitung

  1. stirringThe resulting solution was stirred for 4 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed again with water, saturated K2CO3 solution
  4. dry with materialdried with MgSO4
  5. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-34728028b01f47d2ac4cf2ff27836909
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762551

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