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

HRID 1739355Notes

Reaction equation

HRID 1739355 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9b2b6c6b468d45d1aa0fee130f2bb599
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

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