Sodium Carbonate → HCID 18448471, compound

HRID 1269547Notes

Reaction equation

HRID 1269547 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2].C(B(CC)[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[C:8]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 1235464-Bromo-2-nitrotolueneHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 18448471HCID 18448471, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Nitro-4-bromotoluene (8.74 g, 40.46 mmol) was dissolved in 75 mL dioxane and 25 mL water to which was added diethyl-(3-pyridyl)borane (5.95 g, 40.46 mmol), sodium carbonate (8.58 g, 80.91 mmol) and tetrakis(triphenylphosphine palladium(0) (0.94 g, 0.81 mmol). The mixture was heated at reflux for 18 h then cooled to ambient temperature. The mixture was diluted with 600 mL water and extracted with diethyl ether (2×300 mL). The organic phases were combined and extracted with 0.3 N HCl (3×200 mL). The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (2×300 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 6.39 g (74%) of 2-nitro-4-(3-pyridyl)toluene as a brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. extractionextracted with diethyl ether (2×300 mL)
  4. extractionextracted with 0.3 N HCl (3×200 mL)
  5. extractionThe acidic extractions
  6. extractionThis basic layer was extracted with diethyl ether (2×300 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91f8fdc22d934ee1852675970bb314e9
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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