Triphenylphosphine → 2,7-difluoro-9H-carbazole

HRID 1776196Notes

Reaction equation

HRID 1776196 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)[NH:15][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 3454114,4'-Difluoro-2-nitro-1,1'-biphenyl

Product 1

HCID 593261412,7-difluoro-9H-carbazoleYield 82%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 4,4′-difluoro-2-nitro-1,1′-biphenyl (0.580 g, 2.5 mmol) and triphenylphosphine (1.617 g, 6.2 mmol) in anhydrous 1,2-dichlorobenzene (5 mL) was heated to 175° C. in a microwave reactor for 4 hrs. The mixture was cooled to room temperature and concentrated to a black residue under high vacuum. The crude product was purified by silica gel chromatography (5-50% methylene chloride/hexanes) to afford the product as a light brown powder (0.41 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 8.10 (br s, 1H), 7.93 (dd, 2H, J=8.7, 5.4 Hz), 7.11 (dd, 2H, J=9.3, 2.4 Hz), 6.99 (ddd, 2H, J=9.6, 9.0, 2.4 Hz).

Workup

  1. concentrationconcentrated to a black residue under high vacuum
  2. customThe crude product was purified by silica gel chromatography (5-50% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-3b6fc24c887b4cd6a2171eeef7d61b57
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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