2-Bromo-1-chloro-4-nitrobenzene → 2-(2-Chloro-5-nitrophenyl)pyridine

HRID 922822Notes

Reaction equation

HRID 922822 reaction equation
[Br-].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Zn+].Br[C:10]1[CH:11]=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][C:15]=1[Cl:16]>>[Cl:16][C:15]1[CH:14]=[CH:13][C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1

Participants

3

Reactant 2

HCID 27355492-Bromo-1-chloro-4-nitrobenzeneHCID 178418723HCID 178418723, compound

Product 1

HCID 401519232-(2-Chloro-5-nitrophenyl)pyridine

Procedure

Procedure B was performed with 2-pyridylzinc bromide (4 mL, 2.0 mmol, 0.5 M in THF) and 3-bromo-4-chloro-nitrobenzene (236 mg, 1.0 mmol). Purified by chromatography on silica gel (10% ethyl acetate/hexanes) to yield 2-(2-chloro-5-nitrophenyl)pyridine as a light yellow solid.

Workup

  1. customPurified by chromatography on silica gel (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-630ef5a6db3e46b5bb874ffcbe165be5
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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