Triphenylphosphine → 4,5-difluoro-9H-carbazole

HRID 1776205Notes

Reaction equation

HRID 1776205 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][CH:14]=[CH:13][C:12]=1[F:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[F:1][C:2]1[C:3]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 463126102,2'-Difluoro-6-nitro-1,1'-biphenyl

Product 1

HCID 683967954,5-difluoro-9H-carbazoleYield 44.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 2,2′-difluoro-6-nitro-1,1′-biphenyl (0.740 g, 3.1 mmol) and triphenylphosphine (2.063 g, 7.9 mmol) in anhydrous 1,2-dichlorobenzene (1.5 mL) was heated to 175° C. in a microwave reactor for 3 hrs. The mixture was cooled to room temperature and purified by silica gel chromatography (5-50% methylene chloride/hexanes) to afford the product as a white solid (0.28 g, 44%). 1H NMR (CDCl3, 300 MHz) δ 8.26 (br s, 1H), 7.39 (tt, 2H, J=8.1, 2.4 Hz), 7.22 (d, 2H, J=8.1 Hz), 6.97 (dt, 2H, J=8.1, 5.1 Hz).

Workup

  1. custompurified by silica gel chromatography (5-50% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-a4339df2a691415b82c903799405bb5b
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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