Diethyl Ether → 4-Methyl-2-phenylpyridine

HRID 227209Notes

Reaction equation

HRID 227209 reaction equation
CCOCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Li]CCCC.[CH3:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>[Cl-].[Na+].O>[CH3:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7961BromobenzeneHCID 79634-MethylpyridineHCID 178418339Butyllithium

Product 1

HCID 770264-Methyl-2-phenylpyridineYield 36%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A two necked round-bottom flask (250 mL) containing a stir bar fitted with a reflux condenser was evacuated and purged with nitrogen gas. Dry ether (50 mL) and bromobenzene (0.0191 mol, 3.0 g) were added to the flask followed by the slow addition of n-BuLi (0.0229 mol, 9.17 mL) via a syringe pump. The reaction mixture was stirred at room temperature for 30-40 min and then 4-methyl pyridine (0.0191 mol, 1.779 g) was slowly added. The reaction mixture was then refluxed for 2 to 3 hr. The reaction mixture was then cooled to room temperature, diluted with an aqueous brine solution and extracted with ether (3×30 mL). The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using hexanes/EA as eluent. The desired 4-methyl-2-phenylpyridine was obtained. (1.15 g; 36% yield).

Workup

  1. additionA two necked round-bottom flask (250 mL) containing a stir bar
  2. customfitted with a reflux condenser
  3. customwas evacuated
  4. custompurged with nitrogen gas
  5. temperatureThe reaction mixture was then refluxed for 2 to 3 hr
  6. temperatureThe reaction mixture was then cooled to room temperature
  7. extractionextracted with ether (3×30 mL)
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f7b6e2a49fc44b1dab08cc84e36abd87
Source dataset
uspto-grants-2009_07
Patent number
US07560176B2

Reaction notes

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