Methyl iodide → 5-(2-Fluoro-6-iodophenyl)-2-methyl-2H-tetrazole

HRID 1374156Notes

Reaction equation

HRID 1374156 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[C:9]1[NH:13][N:12]=[N:11][N:10]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[C:9]1[N:10]=[N:11][N:12]([CH3:14])[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505770HCID 178505770, compound

Product 1

HCID 161029015-(2-Fluoro-6-iodophenyl)-2-methyl-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-fluoro-6-iodophenyl)-1H-tetrazole (23.48 g, 80.97 mmol), potassium carbonate (16.79 g, 0.121 mol), and iodomethane (16.09 g, 0.113 mol) in 25 mL DMF was stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water, and the organic extract was washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 0–10% ethyl acetate in hexanes to provide 5-(2-fluoro-6-iodophenyl)-2-methyl-2H-tetrazole that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 305.06 for M+H+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. washeluted with 0–10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-78c3b4c217064f5e9bf6b30eae3f7822
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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