Acetic Acid → tert-Butyl 3-(4-bromophenyl)sulfonylpropionate

HRID 380075

Reaktionsgleichung

Reaktionsgleichung von HRID 380075
[Na+].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[C:12]([O:16][C:17](=[O:20])[CH:18]=[CH2:19])([CH3:15])([CH3:14])[CH3:13].C(O)C.C(O)(=O)C>C(OCC)(=O)C>[C:12]([O:16][C:17](=[O:20])[CH2:18][CH2:19][S:9]([C:6]1[CH:7]=[CH:8][C:3]([Br:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 702EthanolHCID 15458tert-Butyl acrylate2×HCID 23670685Sodium 4-bromobenzene-1-sulfinate

Produkt 1

HCID 17851886tert-Butyl 3-(4-bromophenyl)sulfonylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The mixture of 4-bromophenylsulfinic acid sodium salt (729 mg), 2-propenoic acid t-butyl ester (439 μl), 95% ethanol (4 ml) and acetic acid (372 μl) was stirred for 12 hours at room temperature. Further, 2-propenoic acid t-butyl ester (2.20 ml) was added to the mixture and it was refluxed for 4 hours. The reaction mixture was diluted with ethyl acetate. The mixture was washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (872 mg) having the following physical data.

Aufarbeitung

  1. temperaturewas refluxed for 4 hours
  2. washThe mixture was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-217059bb34c745e680fe5fd722e44144
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300514B1

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