Triphenylphosphine → 2,5-Difluoro-9H-carbazole

HRID 1776199Notes

Reaction equation

HRID 1776199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[F:17][C:14]1[CH:15]=[CH:16][C:11]2[C:3]3[C:4](=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[NH:8][C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 463126122,4'-Difluoro-6-nitro-1,1'-biphenyl

Product 1

HCID 867021382,5-Difluoro-9H-carbazoleYield 88%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 2,4′-difluoro-6-nitro-1,1′-biphenyl (1.100 g, 4.7 mmol) and triphenylphosphine (3.067 g, 11.7 mmol) in anhydrous 1,2-dichlorobenzene (2 mL) was heated to 175° C. in a microwave reactor for 4 hrs. The mixture was cooled to room temperature and concentrated in vacuo. The crude residue was then purified by silica gel chromatography (5-50% methylene chloride/hexanes) to afford the product as a white solid (0.84 g, 88%). 1H NMR (CDCl3, 300 MHz) δ 8.17 (br s, 1H), 8.12 (dd, 1H, J=8.7, 5.1 Hz), 7.33 (td, 1H, J=8.1, 5.1 Hz), 7.20 (d, 1H, J=8.1 Hz), 7.12 (dd, 1H, J=9.3, 2.4 Hz), 7.02 (td, 1H, J=9.3, 2.4 Hz), 6.93 (dd, 1H, J=9.6, 7.8 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was then purified by silica gel chromatography (5-50% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-21c1f9d145ee4ba6b5f9bb364e2000e0
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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