2-Bromo-5-nitroanisole → 2-(2-Methoxy-4-nitrophenyl)pyridine

HRID 746823Notes

Reaction equation

HRID 746823 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].Br[Zn][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C1COCC1>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 1012932-Bromo-5-nitroanisoleHCID 178419760HCID 178419760, compound

Product 1

HCID 219565262-(2-Methoxy-4-nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
63 °C

Procedure

A solution of 1-bromo-2-methoxy-4-nitrobenzene (7 g, 30.17 mmol), bromo(pyridin-2-yl)zinc (80 mL of 0.5M in THF, 40 mmol), tetrakis(triphenlyphosphine)palladium(0) (1.7 g, 1.47 mmol) in 70 mL THF was degassed with nitrogen for 10 minutes, then heated at 63° C. for 6 hr. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7) to give 2-(2-methoxy-4-nitrophenyl)pyridine. MS (ESI) 231 (M++H).

Workup

  1. customThe reaction mixture was quenched with H2O (30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7)

Sources & evidence

ORD record
ord-e07fad909f2f4b59991aca17de8e29cc
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

Loading…