Chloroform → 4-(Dichloromethyl)-2-fluoro-5-nitrobenzotrifluoride

HRID 412078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412078
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].[CH:21](Cl)([Cl:23])[Cl:22].C(O)(=O)C.CO>O1CCCC1.[Cl-].[Na+].O.CCCCCC.C(OCC)(=O)C>[Cl:22][CH:21]([Cl:23])[C:12]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]([C:17]([F:18])([F:19])[F:20])=[C:8]([F:7])[CH:13]=1

Komponenten

9

Edukt 4

HCID 6212ChloroformHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 10129899Acetic acid methanolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 185367484-(Dichloromethyl)-2-fluoro-5-nitrobenzotrifluorideAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of potassium t-butoxide (1.25 g, 11.1 mmol) in tetrahydrofuran (25 ml) was slowly added dropwise a solution of 2-fluoro-5-nitrobenzotrifluoride (1.00 g, 4.78 mmol) and chloroform (599 mg, 5.02 mmol) in tetrahydrofuran (2.5 ml) at −78° C. After stirring for 15 minutes at the same temperature, acetic acid-methanol (1:1, 5 ml) was added and the temperature was raised to room temperature. Ethyl acetate and saturated brine were added to the reaction mixture, which was extracted with ethyl acetate. After washed with brine, the organic layer was dried over anhydrous magnesium sulfate and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [hexane→hexane-ethyl acetate(300:1)] to obtain 714 mg of title compound as pale yellow liquid. Yield 51%.

Aufarbeitung

  1. additionwas added
  2. extractionwas extracted with ethyl acetate
  3. washAfter washed with brine
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate and solvent
  5. distillationwas distilled off
  6. customThe residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-709a237c3984425b80c000aa069b163e
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562839B1

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