2-Bromoanthraquinone → 2-Bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol

HRID 1666030

Reaction equation

HRID 1666030 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([OH:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:2]3[CH:15]=[CH:14][CH:13]=[CH:4][CH:3]=3)([OH:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2210132-BromoanthraquinoneHCID 178506676HCID 178506676, compound

Product 1

HCID 231602182-Bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.9 g (17 mmol) of 2-bromo-9,10-anthraquinone was put in a 300 mL three-neck flask, the atmosphere in the flask was substituted by nitrogen, and 100 mL of tetrahydrofuran (THF) was added thereto and dissolved well. Then, 18 mL (37 mmol) of phenyllithium was dropped into this solution and stirred at room temperature for approximately 12 hours. After reaction, the solution was washed with water, and an aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was concentrated, so that 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol (about 7.6 g), which was the object of the synthesis, was obtained.

Workup

  1. additionwas added
  2. dissolutiondissolved well
  3. customAfter reaction
  4. washthe solution was washed with water
  5. extractionan aqueous layer was extracted with ethyl acetate
  6. dry with materialThe extracted solution and an organic layer were dried with magnesium sulfate
  7. customAfter drying
  8. filtrationthe mixture was subjected to suction filtration
  9. concentrationthe filtrate was concentrated, so that 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol (about 7.6 g), which
  10. customthe object of the synthesis
  11. customwas obtained

Sources & evidence

ORD record
ord-d4d9fcb7ba4b4be090675f508253905e
Source dataset
uspto-grants-2011_10
Patent number
US08040047B2

Linked notes

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