Water → HCID 59506829, Verbindung

HRID 1098509

Reaktionsgleichung

Reaktionsgleichung von HRID 1098509
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[C:4]([F:14])[CH:3]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].O>C1COCC1.C(=O)=O.CC(C)=O>[Cl:1][C:2]1[C:3]([CH:22]=[O:23])=[C:4]([F:14])[C:5]([O:8][CH2:9][C:10]([F:12])([F:11])[F:13])=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 595067484-Chloro-2-fluoro-1-(2,2,2-trifluoroethoxy)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 59506829HCID 59506829, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 18522661Acetone cardiceLösungsmittel

Versuchsvorschrift

To 4-Chloro-2-fluoro-1-(2,2,2-trifluoro-ethoxy)-benzene (522, 0.80 g, 3.5 mmol) in THF (20 mL), cooled in dry ice/acetone bath and under an atmosphere of nitrogen, was slowly added n-butyllithium (1.60 M in Hexane, 2.30 mL). After an hour, N,N-dimethylformamide (0.298 mL, 3.85 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to reach room temperature and was stirred for 10 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the compound (523, 450 mg, 50%).

Aufarbeitung

  1. waitAfter an hour
  2. customto reach room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% ethyl acetate in hexane
  9. customto give the compound (523, 450 mg, 50%)

Quellen und Nachweise

ORD-Eintrag
ord-7ec97d3340554386bfe8aaf04c29536e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143271B2

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