1-(2-Bromo-5-fluorophenyl)-1H-1,2,3-triazole → 4-Fluoro-2-(1H-1,2,3-triazol-1-yl)benzonitrile

HRID 1664183Notes

Reaction equation

HRID 1664183 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][N:11]=[N:10]1.[C:14]([Cu])#[N:15]>CN1C(=O)CCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[N:15])=[C:3]([N:9]2[CH:13]=[CH:12][N:11]=[N:10]2)[CH:4]=1

Participants

4

Reactant 2

HCID 210697641-(2-Bromo-5-fluorophenyl)-1H-1,2,3-triazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 210698774-Fluoro-2-(1H-1,2,3-triazol-1-yl)benzonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1-(2-bromo-5-fluorophenyl)-1H-1,2,3-triazole (0.603 g, 2.49 mmol), CuCN (0.245 g, 2.74 mmol), in 15 mL of NMP was subjected to microwave irradiation at 150° C. for 0.5 h. The brown mixture was filtered over Celite® and washed with DMF. This solution was treated with 10% aqueous NH4OH (28-30% solution) and extracted with EtOAc. The organic fractions were combined and successively washed with 10% aqueous NH4OH (28-30% solution), saturated aqueous NH4Cl, water, brine and dried over Na2SO4. The resulting mixture was concentrated in vacuo and the residue was purified with a Biotage column chromatography system on silica gel with hexanes:ethyl acetate (7:3 to 6:4) gradient as the eluent to afford the title compound as a light yellow solid (0.285 g, 61% yield): 1H NMR (400 MHz, CDCl3) δ: 8.40 (1 H, d, J=1.0 Hz), 7.96 (1H, s), 7.91 (1H, dd, J=8.6, 5.6 Hz), 7.77 (1H, dd, J=8.7, 2.4 Hz), 7.31-7.39 (1H, m).

Workup

  1. customirradiation at 150° C. for 0.5 h
  2. filtrationThe brown mixture was filtered over Celite®
  3. washwashed with DMF
  4. additionThis solution was treated with 10% aqueous NH4OH (28-30% solution)
  5. extractionextracted with EtOAc
  6. washsuccessively washed with 10% aqueous NH4OH (28-30% solution), saturated aqueous NH4Cl, water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationThe resulting mixture was concentrated in vacuo
  9. customthe residue was purified with a Biotage column chromatography system on silica gel with hexanes:ethyl acetate (7:3 to 6:4) gradient as the eluent

Sources & evidence

ORD record
ord-7803a98002884633b944d1ae46df4d4a
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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