Potassium Bicarbonate → 2-(4-bromo-2-nitrothiophen-3-yl)-2H-1,2,3-triazole

HRID 2098079Notes

Reaction equation

HRID 2098079 reaction equation
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH:15]=[CH:14][N:13]=[N:12]1.C(=O)(O)[O-].[K+]>CN(C=O)C>[Br:7][C:6]1[C:2]([N:12]2[N:13]=[CH:14][CH:15]=[N:11]2)=[C:3]([N+:8]([O-:10])=[O:9])[S:4][CH:5]=1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 12015063,4-Dibromo-2-nitrothiopheneHCID 178418936HCID 178418936, compound

Product 1

HCID 687845502-(4-bromo-2-nitrothiophen-3-yl)-2H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,4-dibromo-2-nitrothiophene (1.5 g, 5.23 mmol), 1H-1,2,3-triazole (0.30 mL, 5.18 mmol) and potassium bicarbonate (0.54 g, 5.36 mmol) in DMF (13 mL) were stirred in an oil bath set at 110° C. under condenser with N2 (g) inlet for 1 h. The reaction mixture was quenched with H2O and extracted with ethyl acetate. The organic phase was collected, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane) gave the regio-isomer nitro intermediate of interest (0.518 g, 36%). Retention time (min)=1.950, method [4], MS (ESI) 276.9 (M+H).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was collected
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (silica, 30:70 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f5f7cb4f17f84ef39cf6236eaec88a43
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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