Triethyl Phosphate → 2-Bromo-9H-carbazole

HRID 513318Notes

Reaction equation

HRID 513318 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[CH:3]=1.P(O[CH2:20][CH3:21])(OCC)(OCC)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:20]3[C:21](=[CH:7][CH:2]=[CH:3][CH:4]=3)[NH:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 6535Triethyl PhosphateHCID 11457Benzene, 1-bromo-3-nitro-

Product 1

HCID 127170892-Bromo-9H-carbazole

Procedure

A 250 mL round bottom flask was charged with 4-Bromo-2-nitrobenzene (19.2 g, 69.04 mmol), and triethyl phosphate (84 mL, 483.28 mmol). Then, at 160° C. to 165° C., the mixture was heated under reflux 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.

Workup

  1. temperatureThen, at 160° C. to 165° C., the mixture was heated
  2. temperatureunder reflux 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

Sources & evidence

ORD record
ord-81d33bf85788415fad1de26013e0cba7
Source dataset
uspto-grants-2015_08
Patent number
US09102616B2

Reaction notes

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