Triphenylphosphine → 9H-carbazole-4-carbaldehyde

HRID 659655Notes

Reaction equation

HRID 659655 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH:16]=[O:17])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClC1C=CC=CC=1Cl>[CH:5]1[C:4]2[NH:1][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:8]([CH:16]=[O:17])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 541378936-Nitrobiphenyl-2-carbaldehyde

Product 1

HCID 200308319H-carbazole-4-carbaldehydeYield 56.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A 100-mL round-bottom flask was placed a solution of 6-nitrobiphenyl-2-carbaldehyde (6.2 g, 27.31 mmol, 1.00 equiv) in 1,2-dichlorobenzene (60 mL). To the mixture was added PPh3 (17.9 g, 68.32 mmol, 2.50 equiv) and the mixture was heated to reflux for 30 hours. Upon completion, the resulting mixture was concentrated on a rotary evaporator to give a residue that was purified by silica gel column chromatography affording 9H-carbazole-4-carbaldehyde as yellow solid (3 g, 56%).

Workup

  1. customA 100-mL round-bottom flask was placed
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 30 hours
  4. concentrationUpon completion, the resulting mixture was concentrated on a rotary evaporator
  5. customto give a residue that
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d633bdda07084425ae5b2cbab783e3e4
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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