2-Chloroanthraquinone → HCID 59653499, compound

HRID 2400601Notes

Reaction equation

HRID 2400601 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Li][C:13]([CH3:16])([CH3:15])[CH3:14].Cl[C:18]1[CH:31]=[CH:30][C:29]2[C:28](=O)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=O)[C:20]=2[CH:19]=1>C1COCC1>[CH3:14][C:13]1[CH:16]=[CH:23][C:24]([C:18]2[CH:31]=[CH:30][C:29]3[C:20](=[C:21]([C:31]4[CH:18]=[CH:19][C:20]5[C:29](=[CH:28][CH:27]=[CH:22][CH:21]=5)[CH:30]=4)[C:22]4[C:27]([C:28]=3[C:2]3[CH:11]=[CH:10][C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH:3]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:19]=2)=[CH:25][CH:15]=1

Participants

5

Reactant 3

HCID 85532-ChloroanthraquinoneHCID 113722-BromonaphthaleneHCID 178418306HCID 178418306, compound

Product 1

HCID 59653499HCID 59653499, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Inv-A46, 2-(4-methylphenyl)-9,10-di-2-naphthalenylanthracene was prepared according to equation 1-equation 3. 2-Bromonaphthalene (9.2 g, 44.4 mmol) was dissolved in dry THF (118 ml) and cooled to −78° C. t-BuLi (1.7 M, 52.3 g, 89 mmol) was added in dropwise manner over 5 min, then the reaction was stirred at this temperature for another 5 min. Upon the addition of 2-chloroanthraquinone (4.3 g, 17.8 mmol), the reaction was removed from the acetone-dry ice bath and stirred at room temperature overnight. The reaction mixture was added to aqueous ammonium chloride solution and the product was extracted with methylene chloride. The organic phase was dried with magnesium sulfate, filtered, and concentrated. Purification by crystallization (85% ether/heptane) gave Int-1 (eq. 1).

Workup

  1. additionwas added in dropwise manner over 5 min
  2. customthe reaction was removed from the acetone-dry ice bath
  3. stirringstirred at room temperature overnight
  4. additionThe reaction mixture was added to aqueous ammonium chloride solution
  5. extractionthe product was extracted with methylene chloride
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification
  10. customby crystallization (85% ether/heptane)
  11. customgave Int-1 (eq. 1)

Sources & evidence

ORD record
ord-a5571583146044a8bde1c29d94a3ed6c
Source dataset
uspto-grants-2014_08
Patent number
US08795855B2

Reaction notes

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