Benzyl Alcohol → 2-(Benzyloxy)-3-bromo-6-methylpyridine

HRID 2390808Notes

Reaction equation

HRID 2390808 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)([CH3:8])[NH:6][CH:7]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+]>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[CH2:10]([O:17][C:7]1[C:2]([Br:1])=[CH:3][CH:4]=[C:5]([CH3:8])[N:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 67069981HCID 67069981, compound

Product 1

HCID 670700372-(Benzyloxy)-3-bromo-6-methylpyridineYield 78%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent

Procedure

step 1—A mixture of 5-bromo-2-chloro-2-picoline (4.855 g, 23.51 mmol), benzyl alcohol (2.60 mL, 25.12 mmol), KOH (2.93 g, 52.32 mmol), and 18-crown-6 ether (0.34 g, 1.29 mmol) in toluene (30 mL) was refluxed overnight. The reaction was cooled to RT, diluted with ice water and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with 2% EtOAc/hexanes to afford 5.006 g (78%) of 2-benzyloxy-3-bromo-6-methyl-pyridine (58) as a colorless oil.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by SiO2 chromatography
  9. washeluting with 2% EtOAc/hexanes

Sources & evidence

ORD record
ord-b9651255dd794f69ba5980d850b81393
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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