Trifluoroacetic acid → HCID 23271750, compound

HRID 550331Notes

Reaction equation

HRID 550331 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[C:6]([OH:18])(C)[C:5](O)([CH3:19])[C:4]=2[CH:3]=1.F[C:22](F)(F)C(O)=O>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]([CH3:19])([CH3:22])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23150364HCID 23150364, compound

Product 1

HCID 23271750HCID 23271750, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

132.8 g (294 mmol) of 2,7-dibromo-9,10-dihydroxy-9,10-dimethyl-9,10-dihydrophenanthrene were suspended in 420 ml of acetic acid and 210 ml of trifluoroacetic acid under argon, and the mixture was stirred for 3 h under reflux. After the mixture had been stirred overnight at room temperature, it was filtered with suction, the residue was washed with water and methanol and dissolved in toluene, the solution was filtered through silica gel, and the solvent was removed, giving 89.9 g (80.4% of theory) of the product, which was used without further purification.

Workup

  1. temperatureunder reflux
  2. filtrationit was filtered with suction
  3. washthe residue was washed with water and methanol
  4. dissolutiondissolved in toluene
  5. filtrationthe solution was filtered through silica gel
  6. customthe solvent was removed
  7. customgiving 89.9 g (80.4% of theory) of the product, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-a4969e7452bf4b34b31f6858f721d6e8
Source dataset
uspto-grants-2011_05
Patent number
US07947382B2

Reaction notes

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