Methyl iodide → 5-(2-bromo-4-chloro-6-fluoro-phenyl)-1-methyl-1H-tetrazole

HRID 1404559Notes

Reaction equation

HRID 1404559 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[N:11]=[N:12][NH:13][N:14]=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:14]([CH3:15])[N:13]=[N:12][N:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 679792895-(2-Bromo-4-chloro-6-fluoro-phenyl)-2H-tetrazole

Product 1

HCID 679793335-(2-bromo-4-chloro-6-fluoro-phenyl)-1-methyl-1H-tetrazoleYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-(2-bromo-4-chloro-6-fluoro-phenyl)-2H-tetrazole (4.15 g, 14.95 mmol), K2CO3 (3.1 g, 22.43 mmol) and iodomethane (1.3 ml, 20.94 mmol) in DMF (30 ml) was stirred at 25° C. for 3 h. The mixture was partitioned between EtOAc (80 ml) and water (60 ml), the organic layer was separated, washed with water and brine, dried with Na2SO4 and concentrated. The remaining residue was purified by chromatography (silica gel; hexane/EtOAc 100:0-90:10) to obtain 5-(2-bromo-4-chloro-6-fluoro-phenyl)-1-methyl-1H-tetrazole as pale yellow solid (1.5 g, 35%) and the title compound as reddish liquid (1.7 g, 39%). MS: 291.0 [M+H]+.

Workup

  1. customThe mixture was partitioned between EtOAc (80 ml) and water (60 ml)
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe remaining residue was purified by chromatography (silica gel; hexane/EtOAc 100:0-90:10)

Sources & evidence

ORD record
ord-7d3678795d8c4617949b03ee63bb20e7
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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