Methanol → (4-BROMO-6-METHYL-PYRIDIN-2-YL)-METHANOL

HRID 1908816Notes

Reaction equation

HRID 1908816 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[CH3:9][OH:10]>OS(O)(=O)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:8])[N:5]=[C:6]([CH2:9][OH:10])[CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 67027007(4-BROMO-6-METHYL-PYRIDIN-2-YL)-METHANOL

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-bromo-2-methyl-pyridine (735 mg, 4.14 mmol) in methanol (80 mL) and H2SO4 (20 μL) is heated to reflux. A solution of (NH4)2S2O8 (3.78 g, 16.6 mmol) in water (6.5 mL) is added dropwise to the stirred mixture. Upon completion of the addition, refluxing is continued for 2 h. The mixture is cooled and the reaction is quenched by adding 1 M aq. NaS2O3 solution. The mixture is further diluted with sat. aq. NaHCO3 solution and extracted twice with EA (2×300 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:2 to give (4-bromo-6-methyl-pyridin-2-yl)-methanol (156 mg) as a white solid; LC-MS: tR=0.32 min, [M+1]+=201.93.

Workup

  1. additionUpon completion of the addition
  2. temperaturerefluxing
  3. temperatureThe mixture is cooled
  4. customthe reaction is quenched
  5. additionby adding 1 M aq. NaS2O3 solution
  6. additionThe mixture is further diluted with sat. aq. NaHCO3 solution
  7. extractionextracted twice with EA (2×300 mL)
  8. dry with materialextracts are dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by CC on silica gel eluting with heptane:EA 3:2

Sources & evidence

ORD record
ord-49f55c2ae8464c57bc6b9812b89af511
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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