Methyl iodide → 2-Bromo-3-(methoxymethyl)pyridine

HRID 1517579Notes

Reaction equation

HRID 1517579 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:12]I>O1CCCC1>[Br:1][C:2]1[C:7]([CH2:8][O:9][CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14761460(2-Bromopyridin-3-yl)methanol

Product 1

HCID 197015792-Bromo-3-(methoxymethyl)pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2-bromopyridin-3-yl)methanol (20 g, 106.37 mmoles) in 140 mL of tetrahydrofuran is added 60% sodium hydride in mineral oil (6.38 g, 155.5 mmol) at 0° C. under nitrogen atmosphere. Solution is stirred at 0° C. for 30 minutes. Methyl iodide (7.95 mL, 127.6 mmol) is added over the solution and the mixture is stirred at room temperature overnight. The mixture is quenched by addition of water and the crude is extracted with ethyl acetate. The organic layer is separated, dried over magnesium sulfate and solvent evaporated in vacuo to afford 2-bromo-3-(methoxymethyl)pyridin in a 98% yield that is used with no further purification. MS (m/z): 202 (M+1), 204 (M+3).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. customThe mixture is quenched by addition of water
  3. extractionthe crude is extracted with ethyl acetate
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate and solvent
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9363cfda6fe34f7cb6971e71c9e0006e
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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