Sodium Carbonate → 4-(4-Methylpyridin-2-yl)-2-nitrotoluene

HRID 1060006Notes

Reaction equation

HRID 1060006 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27340872-Bromo-4-methylpyridineHCID 27735154-Methyl-3-nitrobenzeneboronic acid

Product 1

HCID 186676474-(4-Methylpyridin-2-yl)-2-nitrotolueneYield 66.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-bromo-4-methylpyridine (5.16 g), 4-methyl-3-nitrophenylboronic acid (7.06 g) and tetrakis(triphenylphosphine)-palladium (1.73 g) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (39 ml). The mixture was stirred at 80° C. for 12 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. 2-Propanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methylpyridin-2-yl)-2-nitrotoluene (4.54 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. addition2-Propanol was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ec156ab6696549b1b4493ee408195167
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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