Triethyl Phosphate → 2-bromo-9-ethyl-9H-carbazole

HRID 1473732Notes

Reaction equation

HRID 1473732 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1.P(OCC)(OCC)(O[CH2:20][CH3:21])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:14][C:4]=2[CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:14]([CH2:20][CH3:21])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6535Triethyl PhosphateHCID 218576474'-Bromo-2-nitrobiphenyl

Product 2

HCID 106836922-bromo-9-ethyl-9H-carbazoleHCID 127170892-Bromo-9H-carbazole

Procedure

17.93 g (64.47 mmol) of 4′-bromo-2-nitrobiphenyl and 56.09 mL (322.37 mmol) of triethyl phosphate were put into a round bottom flask under nitrogen, and then refluxed and agitated for 5 hours. After the reaction was finished, the solvent was removed by distillation, and the column was used at a ratio of hexane:MC=3:2 (v/v) to obtain 7.2 g of 2-bromo-9H-carbazole and 4.26 g of 2-bromo-9-ethyl-9H-carbazole.

Workup

  1. temperaturerefluxed
  2. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-470c0d91e1ad4385838ae0db59790734
Source dataset
uspto-grants-2015_04
Patent number
US09017829B2

Reaction notes

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