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

HRID 2213095Notes

Reaction equation

HRID 2213095 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-].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Zn+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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:16]=[CH:17][CH:18]=[CH:19][N:14]=1

Participants

5

Reactant 2

HCID 1012932-Bromo-5-nitroanisoleHCID 178418723HCID 178418723, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromo-5-nitroanisole (5.8 g, 25 mmol) in THF (50 mL) was treated with 2-pyridyl-zinc bromide (50 mL of a 0.5M solution in THF, 25 mmol) and Pd(PPh3)4 (1.44 g, 1.25 mmol). The reaction mixture was degassed by bubbling argon through the solution for min and was subsequently heated to reflux for 12 h while under an atmosphere of argon. The cooled reaction mixture was concentrated and purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:19 to 2:3) to afford the desired 2-(2-methoxy-4-nitrophenyl)pyridine.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling argon through the solution for min
  3. temperaturewas subsequently heated
  4. temperatureto reflux for 12 h while under an atmosphere of argon
  5. customThe cooled reaction mixture
  6. concentrationwas concentrated
  7. custompurified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:19 to 2:3)

Sources & evidence

ORD record
ord-90633e76986b47c095dae0ecbc32a69a
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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