Triphenylphosphine → 2-chloro-9H-carbazole

HRID 1052920Notes

Reaction equation

HRID 1052920 reaction equation
[Cl: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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[Cl: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

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 2355494'-Chloro-2-nitro-1,1'-biphenyl

Product 1

HCID 27523882-chloro-9H-carbazoleYield 93.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Next, a mixed solution of 22 g of 2-(4-chlorophenyl)nitrobenzene, 61 g of triphenylphosphine and 190 ml of o-dichlorobenzene was refluxed for 6 hours under a nitrogen flow. The solution was cooled to room temperature, o-dichlorobenzene was then distilled away under reduced pressure, and the concentrate was purified by silica gel column chromatography, and vacuum-dried to obtain 17.7 g of 2-chloro-9H-carbazole.

Workup

  1. distillationo-dichlorobenzene was then distilled away under reduced pressure
  2. customthe concentrate was purified by silica gel column chromatography
  3. customvacuum-dried

Sources & evidence

ORD record
ord-c705fbb6b51943989e25bee17650b5b6
Source dataset
uspto-grants-2016_07
Patent number
US09391288B2

Reaction notes

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