p-Toluenesulfonic acid → 1-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

HRID 500117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500117
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([OH:11])[OH:10])=[CH:4][C:3]=1[F:13].O=[CH:15][CH:16]=O.C([O-])([O-])O[CH2:20][CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([O:10][CH2:15][CH3:16])[O:11][CH2:20][CH3:21])=[CH:4][C:3]=1[F:13]

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 7860GlyoxalHCID 53630039EthylorthoformateHCID 575165211-(4-Bromo-3-fluorophenyl)-2,2-dihydroxyethanone

Produkt 1

HCID 575165221-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 1-(4-bromo-3-fluorophenyl)-2,2-dihydroxyethanone or 4-bromo-3-fluorophenyl)(oxo)acetaldehyde (7.0 g, 28 mmol) in toluene (50 mL) was added ethyl orthoformate (12 mL, 70 mmol) and p-toluenesulfonic acid (200 mg, 1 mmol). The reaction mixture was refluxed for 4 h. The reaction mixture was cooled to RT, diluted with ethyl acetate, washed with aqueous sodium bicarbonate, water, brine, and dried over magnesium sulfate. Concentration under reduced pressure gave the desired product which was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. washwashed with aqueous sodium bicarbonate, water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-395c3aaa90f342b8b738a94ddc67ad38
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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