1,2-Dimethoxyethane → 2-Chloro-4-(4-methylphenyl)pyridine

HRID 1844927Notes

Reaction equation

HRID 1844927 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[C:9]1([CH3:24])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][C:9]([CH3:24])=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 15165112-Chloro-4-iodopyridineHCID 23005382(2'-Methyl-[1,1'-biphenyl]-4-yl)boronic acid

Product 1

HCID 446052162-Chloro-4-(4-methylphenyl)pyridineYield 44%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-iodopyridine (10.0 g, 41.8 mmol), p-tolylphenylboronic acid (5.68 g, 41.8 mmol), Pd(Ph3P)4 (1.45 g 1.25 mmol), sodium carbonate (13.3 g, 125 mmol), DME (300 mL) and water (75 mL) was degassed with nitrogen and then refluxed overnight. The mixture was concentrated and the extracted with ethyl acetate. The the ethyl acetate layer was dried on Na2SO4, vacuum distilled and recrystalized to give 2-chloro-4-(p-tolyl)pyridine (3.75 g, 18.4 mmol, 44% yield).

Workup

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationThe mixture was concentrated
  4. extractionthe extracted with ethyl acetate
  5. dry with materialThe the ethyl acetate layer was dried on Na2SO4, vacuum
  6. distillationdistilled
  7. customrecrystalized

Sources & evidence

ORD record
ord-4b29de4732e149f8a3225f9d2997d4bc
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

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