2-Bromopyridine → 2-(3-Methoxyphenyl)pyridine

HRID 2117811Notes

Reaction equation

HRID 2117811 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([Mg]Br)[CH:11]=[CH:12][CH:13]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[Cl-].[NH4+]>[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178490745HCID 178490745, compound

Product 1

HCID 27597152-(3-Methoxyphenyl)pyridineYield 96.9%

Reagents, catalysts & solvents 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickelCatalystHCID 3283Diethyl EtherSolvent

Procedure

A tetrahydrofuran solution of 3-methoxyphenyl magnesium bromide (52.4 ml, 1.0 M, 52.4 mmol) was dropwise added to a mixture of 2-bromopyridine (5.0 ml, 52.4 mmol), 1,3-bis(diphenylphosphino)propane nickel (II) chloride (284 mg) and diethyl ether (100 ml) at room temperature while 1 hour. Thereafter, this reaction mixture was poured into an aqueous ammonium chloride solution, the mixture was extracted with toluene, the solvent was distilled off, and the residue was purified by silica gel column chromatography, thereby obtaining 9.4 g of 2-(3-methoxyphenyl)pyridine as colorless oil.

Workup

  1. extractionthe mixture was extracted with toluene
  2. distillationthe solvent was distilled off
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4155883b109d406ba4764295f8497d67
Source dataset
uspto-grants-2008_10
Patent number
US07442797B2

Reaction notes

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