Methyl iodide → 5-(2-bromo-4-chloro-6-fluoro-phenyl)-2-methyl-2H-tetrazole

HRID 1160601Notes

Reaction equation

HRID 1160601 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[NH:14][N:13]=[N:12][N:11]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[N:11]=[N:12][N:13]([CH3:15])[N:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505825HCID 178505825, compound

Product 1

HCID 684526405-(2-bromo-4-chloro-6-fluoro-phenyl)-2-methyl-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the above tetrazole (16.0 g, 57.7 mmol), potassium carbonate (12.0 g, 86.5 mol), and iodomethane (11.5 g, 80.7 mol) in 15 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 the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 293.0 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-1855746ac1b94ec4aa1c8a4311f90c3a
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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