Ethyl Acetate → 2-Bromo-1-[(2,2-diethoxyethyl)thio]-4-chlorobenzene

HRID 2199694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2199694
C(=O)([O-])[O-].[K+].[K+].CO[CH:9](OC)[CH2:10]Br.[Br:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[SH:22].[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>CN(C=O)C.O>[Br:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[S:22][CH2:24][CH:23]([O:25][CH2:9][CH3:10])[O:26][CH2:27][CH3:28]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 218168372-Bromo-4-chlorobenzene-1-thiol

Produkt 1

HCID 670034092-Bromo-1-[(2,2-diethoxyethyl)thio]-4-chlorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Potassium carbonate (0.926 g, 9.34 mmol) then bromoacetaldehyde dimethyl acetal (1.35 g, 6.85 mmol) were added to a solution of 2-bromo-4-chlorobenzenethiol (1.397 g, 6.23 mmol) in anhydrous DMF (11 mL). The mixture was heated at 70° C. for 3 hours. After being allowed to cool to room temperature, the mixture was diluted with ethyl acetate and water. The resulting layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organics were washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The resulting light yellow oil was used directly for the following step. 1H NMR (500 MHz, CDCl3) δ 7.57 (d, J=2.0 Hz, 1H); 7.33 (d, J=8.5 Hz, 1H); 7.26 (dd, J=8.5, 2.0 Hz, 1H); 4.70 (t, J=5.5 Hz, 1H); 3.75-3.68 (m, 2H); 3.61-3.55 (m, 2H); 3.15 (d, J=5.5 Hz, 2H); 1.23 (t, 7.0 Hz, 6H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe resulting layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organics were washed with water
  5. dry with materialsaturated NaCl (aq), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-243693533667479381d774eb63432a1f
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359339B2

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