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20th September 2012 @ 04:22
Upscaled synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate for further synthesis into a sulfonamide.


Reaction start time: 11:30 AM EST 20/9/12
Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1Hpyrrole (0.75 g, 4.0 mmol, 1 equiv) and Sulfur trioxide pyridine (1.9 g, 12 mmol, 3 equiv) were refluxed in toluene (6 mL) for 20 hours.

The toluene was then decanted out and water (10 mL) was added to the solid, followed by heating. To the boiling solution Sodium Carbonate (2 g) was added. The solution was concentrated under reduced atmosphere to give a crude brown and white precipitate. The product was extracted by boiling the crude precipitate in a water:ethanol (20 mL, 10:90) solution for 1 hour followed by filtration. The filtrate was left to cool to room temperature at which point precipitate formed. The precipitate was filtered and washed with ethanol leaving white, powdery solid behind (1.0 g, 86% yield, 3.4 mmol).

See also:
Method used from this paper
Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-1)

Risk and Hazard assessment:
Same as MD 6-1 except increased quantities of reagents
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