Sodium Carbonate → 3-(4-methylphenyl)pyridine

HRID 1349008Notes

Reaction equation

HRID 1349008 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.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>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)[CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 79799Tolylboronic acid

Product 1

HCID 41331893-(4-methylphenyl)pyridineYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 4-tolylboronic acid (38 g, 0.28 mol), 3-bromopyridine (44 g, 0.28 mol), Na2CO3 (200 g) in toluene (500 ml) and water (500 ml) was added Pd(PPh3)4 (16 g, 0.014 mol), and refluxed for 16 h. The reaction mixture was cooled, and the separated organic layer was washed with water and brine, and dried. The solvent was removed to give 4-(3-pyridyl)toluene (42 g, 90%).

Workup

  1. temperaturerefluxed for 16 h
  2. temperatureThe reaction mixture was cooled
  3. washthe separated organic layer was washed with water and brine
  4. customdried
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-5aeb75ef1b9245f8bf3a77cd781d6baf
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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