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

HRID 1519866Notes

Reaction equation

HRID 1519866 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-77f5252a856b48a8bac80f47c5616223
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

Loading…