1,3-Dibromobenzene → 2-(3-bromophenyl)-2H-1,2,3-triazole

HRID 881982Notes

Reaction equation

HRID 881982 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[NH:9]1[CH:13]=[CH:12][N:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[Br:8][C:4]1[CH:3]=[C:2]([N:10]2[N:11]=[CH:12][CH:13]=[N:9]2)[CH:7]=[CH:6][CH:5]=1.[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][N:11]=[N:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 79271,3-DibromobenzeneHCID 10796Cesium carbonateHCID 178418936HCID 178418936, compound

Product 2

HCID 124615962-(3-bromophenyl)-2H-1,2,3-triazoleHCID 131061071-(3-Bromophenyl)-1H-1,2,3-triazole

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To solution of 1,3-dibromobenzene (84 g, 356 mmol) in DMF (700 ml) was added 1,2,3-1H-triazole (30 g, 427 mmol), Cul (6.8 g, 35.6 mmol), Iron(III) acetylacetonate (38 g, 107 mmol) and cesium carbonate (231 g, 712 mmol). The resulting mixture was heated to 120° C. under a nitrogen atmosphere overnight. After cooling to room temperature the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified using normal phase chromatography eluting with petroleum ether containing 20% ethyl acetate to give 2-(3-bromophenyl)-2H-1,2,3-triazole (28 g) and 1-(3-bromophenyl)-1H-1,2,3-triazole (11 g) as the pure isomers.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified
  5. washeluting with petroleum ether containing 20% ethyl acetate

Sources & evidence

ORD record
ord-b8787cc911c0473398dee315c10e7939
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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