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

HRID 2062134Notes

Reaction equation

HRID 2062134 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 into a 300 mL three-neck flask. The atmosphere in the flask was substituted with nitrogen. 100 mL of tetrahydrofuran (THF) was added and dissolved well. After that, 18 mL (37 mmol) of phenyl lithium was dripped into the solution, and the mixture was stirred at room temperature for about 12 hours. After the reaction, the solution was washed with water. Then, the aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were mixed to be dried with magnesium sulfate. After the drying, this mixture was suction-filtrated and the filtrate was concentrated, so that 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol (about 7.6 g), which was an object, was obtained.

Workup

  1. dissolutiondissolved well
  2. customAfter the reaction
  3. washthe solution was washed with water
  4. extractionThen, the aqueous layer was extracted with ethyl acetate
  5. additionThe extracted solution and an organic layer were mixed
  6. dry with materialto be dried with magnesium sulfate
  7. filtrationAfter the drying, this mixture was suction-filtrated
  8. concentrationthe filtrate was concentrated, so that 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol (about 7.6 g), which
  9. customwas obtained

Sources & evidence

ORD record
ord-6cc8bb56db144caf89982002c29ecdc7
Source dataset
uspto-grants-2012_10
Patent number
US08283856B2

Reaction notes

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