5-(2-Bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole → 4-Fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrile

HRID 348133Notes

Reaction equation

HRID 348133 reaction equation
Br[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]([CH3:14])[N:13]=1.[C:15]([Cu])#[N:16]>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]#[N:16])=[C:3]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 210699285-(2-Bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 210698874-Fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrileYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of intermediate 57, 5-(2-bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole (650 mg, 2.53 mmol) and CuCN (224 mg, 2.5 mmol) in dimethylformamide (4 mL) was placed in a sealed tube and heated at 100–110° C. for 20 hrs. After cooling, the insoluble material was filtered, and the filtrate concentrated in vacuo. The residue was dissolved in CH2Cl2, washed with aq. 4N HCl and dil. NH4OH, then dried (MgSO4), filtered, and concentrated. The residual solid was purified by column chromatography (SiO2, CH2Cl2) to obtain 375 mg (Yield 73%) of the title compound as an off-white solid; 1H NMR (500 MHz, CDCl3) δ ppm: 4.48 (3H, s) 7.29 (1H, dd, J=7.6, 2.8 Hz) 7.85 (1H, dd, J=8.6, 5.2 Hz) 8.00 (1H, dd, J=9.0, 2.6 Hz); LC/MS m/z 204.

Workup

  1. customwas placed in a sealed tube
  2. temperatureheated at 100–110° C. for 20 hrs
  3. temperatureAfter cooling
  4. filtrationthe insoluble material was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. washwashed with aq. 4N HCl and dil. NH4OH
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residual solid was purified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-0278533f6e7b4735bf3b8bd7028337c7
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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