p-Bromoacetophenone → 1-[4-(1H-1,2,4-Triazol-1-yl)phenyl]ethan-1-one

HRID 1502770Notes

Reaction equation

HRID 1502770 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)=[O:3].[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.[Cu]I>[N:11]1([C:7]2[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=2)[CH:15]=[N:14][CH:13]=[N:12]1

Participants

7

Reactant 3

HCID 7466p-BromoacetophenoneHCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonate

Product 1

HCID 25603171-[4-(1H-1,2,4-Triazol-1-yl)phenyl]ethan-1-oneYield 96%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromoacetophenone (10 g, 50 mmol) in DMF (100 mL), were added 1,2,4-triazole (5 g, 75 mmol), Cs2CO3 (32.6 g, 100.5 mmol) and CuI (1.4 g, 10.1 mmol) and the resultant reaction mixture was refluxed for 48 h. After completion of the reaction (by TLC), the reaction mixture was cooled to ambient temperature and diluted with water (200 mL) and extracted with EtOAc. The combined organic layer was washed with brine and dried over Na2SO4 and concentrated under reduced pressure. Purification by washing with diethyl ether afforded the title compound as a solid (5 g, 96%): 1H NMR (400 MHz, CDCl3) δ 8.71 (s, 1H), 8.16, (s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.83 (d, J=8.6 Hz, 2H), 2.66 (s, 3H); ESIMS m/z 186.02 ([M−H]−).

Workup

  1. customthe resultant reaction mixture
  2. temperaturewas refluxed for 48 h
  3. customAfter completion of the reaction (by TLC)
  4. extractionextracted with EtOAc
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification
  9. washby washing with diethyl ether

Sources & evidence

ORD record
ord-7a519a3e38dc448687dbd60b7a7d6d89
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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