Triphenylphosphine → 9H-carbazole-2-carbaldehyde

HRID 659645Notes

Reaction equation

HRID 659645 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClC1C=CC=CC=1Cl>[CH:9]1[C:4]2[NH:1][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:5]=2[CH:6]=[CH:7][C:8]=1[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 118170112-Nitrobiphenyl-4-carbaldehyde

Product 1

HCID 121698109H-carbazole-2-carbaldehydeYield 66.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A 250-mL round-bottom flask was charged with 2-nitrobiphenyl-4-carbaldehyde (6.5 g, 28.63 mmol, 1.00 equiv), PPh3 (18.8 g, 71.76 mmol, 2.50 equiv) and 1,2-dichlorobenzene (70 mL). The resulting solution was refluxed for 18 hours. The resulting mixture was concentrated under vacuum. The residue was purified by silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:30) affording 9H-carbazole-2-carbaldehyde as yellow solid (3.7 g, 66%).

Workup

  1. temperatureThe resulting solution was refluxed for 18 hours
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe residue was purified by silica gel column chromatography
  4. washeluted with ethyl acetate/petroleum ether (1:30)

Sources & evidence

ORD record
ord-8d910db0dada4e93814df908abd13f4d
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

Loading…