Methyl iodide → 2-Methyl-5-(4-bromophenyl)tetrazole

HRID 2251201Notes

Reaction equation

HRID 2251201 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)=[CH:4][CH:3]=1.CI.[OH-].[Na+].Cl[CH2:18]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:18])[N:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 7661415-(4-Bromophenyl)-1H-tetrazole

Product 1

HCID 6109772-Methyl-5-(4-bromophenyl)tetrazole

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3.5 mmol of 5-(4-bromo-phenyl)-2H-tetrazole, 0.2 mmol of tetrabutyl ammonium bromide, 4.4 mmol of methyl iodide, 6 ml of 1M aqueous sodium hydroxide and 6 ml of dichloromethane were stirred at room temperature for 24 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried, evaporated and the product purified by column chromatography (SiO2; cyclohexane/ethyl acetate 7:3). MS (m/e): 239.1 (MH+, 29%)

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated
  4. customthe product purified by column chromatography (SiO2; cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-61e50f76e3274c64b24e1a39e172e655
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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