Water → 1-(4-Bromophenyl)-2-phenylethane-1,2-dione

HRID 1595947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595947
Cl(O)(=O)(=O)=O.[OH2:6].O.O.O.[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl.COCCOC>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([C:32]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:6])=[O:31])=[CH:28][CH:29]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24247Perchloric AcidHCID 5197381-(4-Bromophenyl)-2-phenylethanoneHCID 11270721Nitric acid,thallium(3+) salt, trihydrate (9CI)

Produkt 1

HCID 2367011-(4-Bromophenyl)-2-phenylethane-1,2-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Perchloric acid (250 mL), water (250 mL), ethylene glycol dimethyl ether (glyme) (500 mL), thallium (III) nitrate trihydrate (222.0 g, 0.5 mol) and 4-bromodeoxybenzoin (68.75 g, 0.25 mol) are charged to a 2-liter round bottom 3-necked flask equipped with a reflux condenser and a mechanical stirrer. The reaction mixture is heated under nitrogen to reflux for 6 hours. After cooling to ambient temperature, methylene chloride (500 mL) is added. The resulting bilayer is decanted off the precipitated Tl(I) salts formed. The layers are separated and the organic layer is washed with water, saturated aqueous NaHCO3 and brine, followed by recrystallization of the resulting solid from 2-propanol gives the title compound.

Aufarbeitung

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureThe reaction mixture is heated under nitrogen
  3. temperatureto reflux for 6 hours
  4. customThe resulting bilayer is decanted off the precipitated Tl(I) salts
  5. customformed
  6. customThe layers are separated
  7. washthe organic layer is washed with water, saturated aqueous NaHCO3 and brine
  8. customfollowed by recrystallization of the resulting solid from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-af2beb105d0046fb8351b674e61a5cf8
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288188B1

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