Methyl iodide → 3-Bromo-4-(methoxymethyl)pyridine

HRID 712636Notes

Reaction equation

HRID 712636 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[H-].[Na+].[CH3:12]I>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46840038(3-Bromopyridin-4-yl)methanol

Product 1

HCID 667140503-Bromo-4-(methoxymethyl)pyridineYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-bromo-pyridin-4-yl)-methanol (300 mg, 1.6 mmol) in THF (50 mL) at 0° C. is added 60% NaH (96 mg, 2.4 mmol). Then the mixture is stirred at room temperature for 30 min. MeI (270 mg, 1.9 mmol) is added to the mixture at 0° C. and again the mixture is stirred at room temperature for 4 hrs. Then the reaction is quenched with saturated NH4Cl aqueous solution and the mixture is extracted with EtOAc. The organic layer is separated, dried and concentrated to give the crude product. Purification by prep-TLC affords 274 mg of 3-bromo-4-methoxymethyl-pyridine.

Workup

  1. stirringagain the mixture is stirred at room temperature for 4 hrs
  2. customThen the reaction is quenched with saturated NH4Cl aqueous solution
  3. extractionthe mixture is extracted with EtOAc
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification

Sources & evidence

ORD record
ord-a6443b9e53f24762bc23e1c1fa59505e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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