2-Bromonaphthalene → 2-Bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diol

HRID 890836Notes

Reaction equation

HRID 890836 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].[Br:17][C:18]1[CH:31]=[CH:30][C:29]2[C:28](=[O:32])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:33])[C:20]=2[CH:19]=1>C1COCC1.CCCCC>[Br:17][C:18]1[CH:31]=[CH:30][C:29]2[C:28]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=3)([OH:32])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([C:5]3[CH:4]=[CH:9][C:16]4[C:13](=[CH:15][CH:3]=[CH:2][CH:11]=4)[CH:14]=3)([OH:33])[C:20]=2[CH:19]=1

Participants

6

Reactant 3

HCID 113722-BromonaphthaleneHCID 2210132-BromoanthraquinoneHCID 178418306HCID 178418306, compound

Product 1

HCID 222471662-Bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diolYield 93%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromonaphthalene (6.49 g, 31.3 mmol) in dry THF (50 ml) was added dropwise t-BuLi (18.4 ml of a 1.7 M solution in pentane) at −78° C. under nitrogen. After the mixture had been stirred for 30 min, 2-bromoanthraquinone (3.00 g, 10.4 mmol) was added at −78° C. The cooling bath was removed and the mixture was stirred for 2 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl ether (3×50 ml). The combined organic extracts were dried over MgSO4 and concentrated under vacuum. The crude product was slurried in petroleum ether, filtered off with suction, and washed with petroleum ether. After drying, the 2-bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diol (5.30 g, 93%) was obtained.

Workup

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. customThe mixture was quenched with saturated aqueous ammonium chloride solution (50 ml)
  4. extractionextracted with ethyl ether (3×50 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated under vacuum
  7. filtrationfiltered off with suction
  8. washwashed with petroleum ether
  9. customAfter drying

Sources & evidence

ORD record
ord-03bcbf3dd5ef4e5199d1c034360cbe7f
Source dataset
uspto-grants-2006_02
Patent number
US06998487B2

Reaction notes

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