2-Bromoanthraquinone → HCID 69032464, compound

HRID 2045745Notes

Reaction equation

HRID 2045745 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-6b5a96933e5c4c90ae1335344a9ba63f
Source dataset
uspto-grants-2013_11
Patent number
US08592053B2

Reaction notes

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