2-Bromoanthraquinone → HCID 69032464, compound

HRID 1774096Notes

Reaction equation

HRID 1774096 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.C1([Li])C=CC=CC=1>O1CCCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]([OH:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([OH:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2210132-BromoanthraquinoneHCID 178506676HCID 178506676, compound

Product 1

HCID 69032464HCID 69032464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 300 mL three-neck flask was put 4.90 g (17.0 mmol) of 2-bromo-9,10-anthraquinone, and the atmosphere in the flask was replaced with nitrogen. To the flask was added 100 mL of tetrahydrofuran (THF), and 17.8 mL (37.3 mmol) of phenyllithium was dropped into this solution. After the completion of the dropping, this solution was stirred at room temperature for 15 hours. Then, this solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract solution and the organic layer were combined and dried with magnesium sulfate. Then, this mixture was gravity filtered. The obtained filtrate was concentrated to give 2-bromo-9,10-dihydroanthracene-9,10-diol, which was the object of the synthesis.

Workup

  1. customIn a 300 mL three-neck flask was put
  2. additionwas dropped into this solution
  3. washThen, this solution was washed with water
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-dd59f05084fd40e8a62ff253de0a01b5
Source dataset
uspto-grants-2016_02
Patent number
US09257654B2

Reaction notes

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