Iodobenzene → 1-Phenyl-1H-1,2,3-triazole

HRID 1751930Notes

Reaction equation

HRID 1751930 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClCCl>[C:7]1([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:7]1([N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 11575IodobenzeneHCID 178418936HCID 178418936, compound

Product 2

HCID 2700091-Phenyl-1H-1,2,3-triazoleYield 48%HCID 50796302-Phenyl-1,2,3-triazoleYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure A (90° C., 30 hours), 1H-[1,2,3]triazole (87 μL, 1.5 mmol) is coupled with iodo-benzene (112 μL, 1.0 mmol). The crude brown oil was purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes=50/50 then pure dichloro-methane) to provide 60 mg of 2-phenyl-2H-[1,2,3]triazole (41% yield) as an uncolored oil and 70 mg of 1-phenyl-1H-[1,2,3]triazole (48% isolated yield) as a light yellow solid.

Workup

  1. customThe crude brown oil was purified by flash chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-3d993867bd394139bec9be84560cc992
Source dataset
uspto-grants-2015_10
Patent number
US09162953B2

Reaction notes

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