Water → 2-Bromo-3-(isopropoxymethyl)-pyridine

HRID 1517580Notes

Reaction equation

HRID 1517580 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:7][C:8]1[C:13]([CH2:14]Br)=[CH:12][CH:11]=[CH:10][N:9]=1.O>CN(C)C=O>[Br:7][C:8]1[C:13]([CH2:14][O:4][CH:1]([CH3:3])[CH3:2])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 109010782-Bromo-3-(bromomethyl)pyridine

Product 1

HCID 582685582-Bromo-3-(isopropoxymethyl)-pyridineYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of isopropyl alcohol (7.31 mL, 95.65 mmol) in dimethylformamide (50 mL) at 0° C. is added sodium hydride (3.63 g, 90.87 mmol) and the mixture is stirred at room temperature for 30 minutes (this reaction is run using a shield as special protection). Then, 2-bromo-3-bromomethyl-pyridine (6 g, 23.91 mmol) in 10 mL of dimethylformamide is added via syringe and the mixture is stirred at room temperature for 1 h. Water is added and the mixture is extracted with ethyl acetate, washed with brine and water, dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude material is purified by normal phase Isco chromatography using ethyl acetate and hexane as eluent (gradient of 5 to 25% of ethyl acetate) to yield 3.67 g of the title compound. MS (m/z): 230, 232 (M+1, M+3)

Workup

  1. stirringthe mixture is stirred at room temperature for 1 h
  2. extractionthe mixture is extracted with ethyl acetate
  3. washwashed with brine and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude material is purified by normal phase Isco chromatography

Sources & evidence

ORD record
ord-ee819b65e6d34b019dbb10a3f8101b9e
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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