Methyl iodide → 5-(2-Bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole

HRID 1664130Notes

Reaction equation

HRID 1664130 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[NH:13][N:12]=[N:11][N:10]=1.CI.[C:16](=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:10]=[N:11][N:12]([CH3:16])[N:13]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 178505485HCID 178505485, compound

Product 1

HCID 210699285-(2-Bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazoleYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-bromo-5-fluoro-phenyl)-1H-tetrazole (1.0 g, 4.12 mmol; Butt Park Ltd.), methyl iodide (1.12 g, 10 mmol) and potassium carbonate (1.5 g) in DMF (5 mL) was stirred at room temperature for 16 hrs, and the mixture concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, CH2Cl2) to provide 650 mg (2.53 mmol, yield 61%) of the title compound as a white powder (fast-moving 2-Me isomer): TLC, Rf 0.7 (CH2Cl2); 1H NMR (500 MHz, CDCl3) δ 4.45 (3H, s) 7.03-7.11 (1H, m) 7.63 (1H, dd, J=8.9, 3.1 Hz) 7.69 (1H, dd, J=8.9, 5.5 Hz); 13C NMR (126 MHz, CDCl3) δ 39.86 (s) 116.28 (s) 118.66 (d, J=22 Hz) 118.76 (d, J=25 Hz) 130.13 (d, J=8.6 Hz) 135.73 (d, J=8.6 Hz) 161.74 (d, J=247.6 Hz) 163.53 (s); LC/MS m/z 257/259.

Workup

  1. concentrationthe mixture concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-54f38371bd2e47daaaf9d2f7354d180c
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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