Triethyl Phosphate → 9H-Dibenzo[a,c]carbazole, 11-bromo-

HRID 513315Notes

Reaction equation

HRID 513315 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[CH:21]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:4]([N+:22]([O-])=O)[CH:3]=1.P(OCC)(OCC)(OCC)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:21]([NH:22][C:4]=2[CH:3]=1)=[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=31

Participants

3

Reactant 2

HCID 6535Triethyl PhosphateHCID 866699719-(4-Bromo-2-nitrophenyl)phenanthrene

Product 1

HCID 866699729H-Dibenzo[a,c]carbazole, 11-bromo-Yield 62%

Procedure

A 250 mL round bottom flask was charged with 9-(4-bromo-2-nitrophenyl)phenanthrene (26.36 g, 69.69 mmol), and triethyl phosphate (84.84 mL, 487.86 mmol), and the mixture was heated under reflux at 160° C. to 165° C. for 14 hours. After the reaction was completed, the remaining triethyl phosphate was removed by vacuum distillation. The resultant product was diluted with a mixed solvent of MeOH:H2O=1:1, and the produced solid was filtered. The obtained solid was washed with a mixed solvent of MeOH:H2O=1:1, and petroleum ether. The solid was dissolved in methylene chloride, dried with MgSO4, and concentrated, and purified by silica gel column (petroleum ether:methylene chloride=2:1). Then, 14.96 g of a product (62%) was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux at 160° C. to 165° C. for 14 hours
  3. customthe remaining triethyl phosphate was removed by vacuum distillation
  4. additionThe resultant product was diluted with a mixed solvent of MeOH
  5. filtrationH2O=1:1, and the produced solid was filtered
  6. washThe obtained solid was washed with a mixed solvent of MeOH
  7. dissolutionThe solid was dissolved in methylene chloride
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated
  10. custompurified by silica gel column (petroleum ether:methylene chloride=2:1)

Sources & evidence

ORD record
ord-8bc1563d00234692a9a3cc26ca9cf95e
Source dataset
uspto-grants-2015_08
Patent number
US09102616B2

Reaction notes

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