1H-1,2,4-Triazole → 1-(4-Bromo-3,5-dimethylphenyl)-1H-1,2,4-triazole

HRID 237579Notes

Reaction equation

HRID 237579 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:10].[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O1CCCC1.[Cu]I>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:4][C:3]=1[CH3:10]

Participants

7

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium Carbonate2×HCID 207480372-Bromo-5-iodo-1,3-dimethylbenzene

Product 1

HCID 866972431-(4-Bromo-3,5-dimethylphenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-bromo-5-iodo-1,3-dimethylbenzene (500 mg), 1,2,4-triazole (340 mg), potassium carbonate (770 mg), and copper(I) iodide (232 mg) in N-methyl-2-pyrrolidinone is stirred at 130° C. over night. More potassium carbonate (770 mg) and copper(I) iodide (232 mg) are added and the mixture is heated to 150° C. for 4 h. After cooling to room temperature the mixture is diluted with tetrahydrofuran and filtered. The filtrate is concentrated in vacuo and purified by HPLC on reversed phase to give the title compound. LC (method 7): tR=0.99 min; Mass spectrum (ESI+): m/z=252, 254 [M+H]+.

Workup

  1. temperaturethe mixture is heated to 150° C. for 4 h
  2. temperatureAfter cooling to room temperature the mixture
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. custompurified by HPLC on reversed phase

Sources & evidence

ORD record
ord-b98bb9696f9d46da995aab369deb0b92
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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