2-Bromo-5-bromomethylpyridine → 2-Bromo-5-(methoxymethyl)pyridine

HRID 1016006Notes

Reaction equation

HRID 1016006 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CO.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:11][CH3:10])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 64246602-Bromo-5-bromomethylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 533855212-Bromo-5-(methoxymethyl)pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-5-bromomethyl-pyridine, 4 (3.58 g, 14.3 mmoles) was dissolved in methanol (20 mL) under nitrogen. Sodium methoxide (0.89 g, 15.7 mmoles, 95%) was added and the mixture stirred at room temperature. After 3 hours, the methanol was rotovapped off and the residue dissolved in dichloromethane and washed with water. The organic extract was adsorbed onto silica gel and chromatographed. The column was eluted with a gradient of hexane to 20% ethyl acetate/hexane. Pure fractions were combined and concentrated to provide the title compound as a colorless oil, 2.62 g (90%). LC/MS (positive ion) m/z=202.0, 204.0 (M+H)+.

Workup

  1. washwashed with water
  2. extractionThe organic extract
  3. customchromatographed
  4. washThe column was eluted with a gradient of hexane to 20% ethyl acetate/hexane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ddd0f25764847548f5581c9365406e6
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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