Methyl iodide → 5-bromo-2-(methoxymethyl)Pyridine

HRID 2170034Notes

Reaction equation

HRID 2170034 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:12]I>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][CH3:12])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 540443575-bromo-2-(methoxymethyl)PyridineYield 102.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of this (5-bromo-pyridin-2-yl)-methanol (4.80 g, 23.0 mmol) in DMF (25 mL) was added drop wise over 5 minutes to a slurry of sodium hydride (1.10 g, 27.8 mmol) in DMF (50 mL) at 0° C. under N3. The mixture was stirred for 15 minutes before the drop wise addition of a solution of methyl iodide (1.57 mL, 25.3 mmol) in DMF (25 mL). The mixture was allowed to reach room temperature and was then stirred overnight. The mixture was poured into brine and extracted with EtOAc. The combined organic layers were thoroughly washed with brine, dried over MgSO4 and evaporated to dryness to give the title compound as a yellow oil (4.77 g, 98%) sufficiently pure for the next step.

Workup

  1. customto reach room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were thoroughly washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3c4f4d40391545909f27dd21eef5618c
Source dataset
uspto-grants-2015_06
Patent number
US09050327B2

Reaction notes

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