2-Bromopyridine → 2-(2-Nitrophenyl)pyridine

HRID 1816285Notes

Reaction equation

HRID 1816285 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br)([O-:3])=[O:2].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>CS(C)=O.N.[Cu].[Pd](Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([O-:3])=[O:2]

Participants

7

Reactant 2

HCID 79732-BromopyridineHCID 113411-Bromo-2-nitrobenzene

Product 1

HCID 2316022-(2-Nitrophenyl)pyridineYield 22%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 24290Palladium ChlorideCatalystHCID 222AmmoniaSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-nitrobromobenzene (2.02 g), 2-bromopyridine (0.80 g), copper powder (1.29 g), and palladium dichloride (0.049 g) in 15 mL of DMSO was heated at 120° C. under N2 for 2 hours. Once cooled, the mixture was diluted with 100 mL of 10% aqueous ammonia and stirred for 30 min. This mixture was filtered, and the filtrate was extracted several times with CHCl3. The combined extracts were dried (Na2SO4) and evaporated. The crude product was purified by chromatography on silica gel with 20% EtOAc/hexanes to yield 0.12 g (22%) of 2-(2-Nitrophenyl)pyridine. [This compound was reported by Molina, Pedro; Lorenzo, Angeles; Aller, Enrique; Tetrahedron; 1992, 48, (22), 4601-4616.]

Workup

  1. temperatureOnce cooled
  2. filtrationThis mixture was filtered
  3. extractionthe filtrate was extracted several times with CHCl3
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-a8948701848c43f59746aececf9873cb
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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