1-Bromoanthraquinone → HCID 66702141, compound

HRID 926676Notes

Reaction equation

HRID 926676 reaction equation
[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[Br:1][C:2]1[C:15]2[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([OH:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([C:2]3[CH:15]=[CH:6][CH:5]=[CH:4][CH:3]=3)([OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 124441-BromoanthraquinoneHCID 178506676HCID 178506676, compound

Product 1

HCID 66702141HCID 66702141, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.37 g (32.4 mmol) of 1-bromoanthraquinone was put into a 500 mL three neck-flask, and the atmosphere of the flask was substituted with nitrogen. 150 mL of tetrahydrofuran (abbreviation: THE) was added to the flask, and then 34.0 mL (71.3 mmol) of phenyllithium (2.1 mol/L dibutyl ether solution) was added in one portion. The solution was stirred for 24 hours at room temperature. After the reaction was completed, the reaction solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted part was combined with the organic layer, and then dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was concentrated, resulting in 14.4 g of 1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol as a brown, oily compound in 100% yield.

Workup

  1. washthe reaction solution was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customAfter drying
  5. filtrationthe mixture was subjected to suction filtration
  6. concentrationthe filtrate was concentrated
  7. customresulting in 14.4 g of 1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol as a brown, oily compound in 100% yield

Sources & evidence

ORD record
ord-89e1cac84d6d4d9b81332ffb025c43f6
Source dataset
uspto-grants-2016_03
Patent number
US09287511B2

Reaction notes

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