Ethyl Acetate → HCID 18979100, Verbindung

HRID 1423098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423098
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8]2.[Br:17]Br.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O>CO>[Br:17][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[N:11]2

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 614880HCID 614880, Verbindung

Produkt 1

HCID 18979100HCID 18979100, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

The intermediate 8-methoxy-2-(trifluoromethyl)quinoline (2.21 g, 9.7 mmol) in MeOH (15 mL) was treated with a 1.5 N solution of bromine in MeOH (7.8 mL, 11.7 mmol) over a 15 min period. This mixture was stirred 2 h then treated with a 1 N aqueous solution of Na2S2O3 (30 mL) and EtOAc (300 mL). The phases where separated and the organic portion washed with brine, a saturated aqueous solution of NaHCO3, and again with brine. The organic phase was dried with Na2SO4, filtered, and evaporated to afford titled compound as a light brown solid. 1H NMR (CDCl3) 8.70 (dd, J=8.8, 0.6, 1H), 7.86 (d, J=8.8, 1H), 7.85 (d, J=8.4, 1H), 7.02 (d, J=8.4, 1H), 4.10 (s, 3H). LC/MS (Method B) 3.82 min, [M+1]+ 305/307.

Aufarbeitung

  1. customThe phases where separated
  2. washthe organic portion washed with brine
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dc4869379f8a43f4a1e93a289a973b0a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927546B2

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