Trifluoroacetic anhydride → 7,8-Dichlorothiochroman-4-one

HRID 865294

Reaktionsgleichung

Reaktionsgleichung von HRID 865294
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][C:12]([OH:14])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.CCCCCC>FC(F)(F)C(O)=O>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]2[C:4]([C:12](=[O:14])[CH2:11][CH2:10][S:9]2)=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 21226206Ethyl acetate hexaneHCID 218490133-(2,3-Dichlorophenylthio)propanoic acid

Produkt 1

HCID 544217637,8-Dichlorothiochroman-4-oneAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

The 3-(2,3-dichlorophenylthio)propanoic acid from Step 1 (3.88 g, 15 mmol) was dissolved in trifluoroacetic acid (10 mL), treated with trifluoroacetic anhydride (5 mL) and stirred at room temperature for 68.2 hours. The reaction mixture was poured into 10% Na2CO3 (100 mL), extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo to give a yellow oil. The crude material was passed through a column of silica gel eluting with 40% ethyl acetate/hexane to give 7,8-dichlorothiochroman-4-one as a white solid (0.46 g, 13%): mp 93°-102° C.; 1H NMR (CDCl3) 300 MHz 7.99 (d, J=8.7 Hz, 1H) 7.27 (d, J=8.7 Hz, 1H) 3.25 (m, 2H) 2.97 (m, 2H). Mass spectrum: M+=233.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-5039621a26814ae9b1fad7f50a43d8ce
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565482

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