2-Bromopyridine → 2-(2-methoxyphenyl)pyridine

HRID 2261499Notes

Reaction equation

HRID 2261499 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.C(COC)OC.O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

10

Reactant 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 2316052-(2-methoxyphenyl)pyridineYield 95%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromopyridine (4.28 mL, 43.9 mmol), 2-methoxyphenylboronic acid (6.7 g, 43.9 mmol), palladium acetate (0.14 g, 0.62 mmol), triphenylphosphine (0.6 mg, 2.3 mmol) and potassium phosphate (9.40 g, 44.3 mmol) were added to a flask. A mixture solution of 10 mL of water and 40 mL of dimethoxyethane was added and reflux was performed for 6 hours. After cooling to room temperature, aqueous ammonium chloride solution (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated. After extracting the residue using diethyl ether, the collected organic layer was dried with magnesium sulfate. After removing volatile materials, followed by purification via silica gel chromatography using n-hexane, 7.7 g (yield: 95%) of 2-(2′-methoxyphenyl)pyridine was obtained as colorless liquid.

Workup

  1. temperaturereflux
  2. customThe organic layer was separated
  3. extractionAfter extracting the residue
  4. dry with materialthe collected organic layer was dried with magnesium sulfate
  5. customAfter removing volatile materials
  6. customfollowed by purification via silica gel chromatography

Sources & evidence

ORD record
ord-444e372e5ec849beb3e64887eef7ddb7
Source dataset
uspto-grants-2010_12
Patent number
US07847039B2

Reaction notes

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