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

HRID 1820745Notes

Reaction equation

HRID 1820745 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-70004881b1454346929063ab3147128b
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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