Triphenylphosphine → HCID 86702141, compound

HRID 1776208Notes

Reaction equation

HRID 1776208 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[F:14][C:12]1[CH:11]=[CH:10][C:9]2[NH:15][C:4]3[C:3]([C:8]=2[CH:13]=1)=[C:2]([F:1])[CH:7]=[CH:6][CH:5]=3

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 46312613HCID 46312613, compound

Product 1

HCID 86702141HCID 86702141, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 2′,5-difluoro-2-nitro-1,1′-biphenyl (1.400 g, 6.0 mmol) and triphenylphosphine (3.903 g, 14.9 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 purified by silica gel chromatography (5-50% methylene chloride/hexanes) to afford the product as a light brown solid (0.62 g, 51%). 1H NMR (CDCl3, 300 MHz) δ 8.12 (br s, 1H), 7.87 (dd, 1H, J=9.0, 2.4 Hz), 7.41-7.31 (m, 2H), 7.24-7.15 (m, 2H), 6.91 (dd, 1H, J=10.2, 8.1 Hz).

Workup

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

Sources & evidence

ORD record
ord-6478f6b6487a49d99f087884ecac449d
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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