Water → HCID 59506829, Verbindung

HRID 1261149

Reaktionsgleichung

Reaktionsgleichung von HRID 1261149
[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-6d4ed904797c4aee83e47f1342eb4f7f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470818B2

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