1-Bromo-4-nitrobenzene → 3-(4-Nitrophenyl)pyridine

HRID 2218114Notes

Reaction equation

HRID 2218114 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1>CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 2

HCID 114661-Bromo-4-nitrobenzeneHCID 27343783-Pyridinylboronic acid

Product 1

HCID 2315043-(4-Nitrophenyl)pyridine

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

1,1′-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.2 g, 0.2 mmol) was added to a stirred and degassed solution of 4-bromonitrobenzene (5 g, 24.8 mmol) and pyridine-3-boronic acid (3.4 g, 27.2 mmol) in dimethyl formamide (50 mL) and 2N sodium carbonate solution in water (20 mL). The reaction mixture was stirred at 100° C. for 18 hours, then allowed to cool. The solution was filtered through celite (Diatomaceous Earth), then ethyl acetate (200 mL) was added and the organic phase was washed three time with brine (200 mL). The organic was dried (anhydrous magnesium sulfate), concentrated and purified by chromatography on silica gel (30% v/v ethyl acetate in petroleum ether) to afford the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 18 hours
  2. temperatureto cool
  3. filtrationThe solution was filtered through celite (Diatomaceous Earth)
  4. additionethyl acetate (200 mL) was added
  5. washthe organic phase was washed three time with brine (200 mL)
  6. dry with materialThe organic was dried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel (30% v/v ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-fa115b3a6cd34574a09fe228ed357567
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

Loading…