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31st January 2013 @ 17:13

Could only isolate starting material, reaction is to be redone with AEW 1-1.

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Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate with reduced sulfur trioxide pyridine complex.

Reaction start time: 12:30 AM EST 26/1/13

MD 22-1 (3.25 g, 10 mmol, 1 equiv) and Sulfur trioxide pyridine (2.6 g, 10 mmol, 1 equiv) were refluxed in toluene (6 mL) for 16 hours. Reaction was concentrated under reduced atmosphere followed by addition of water and heating to 100° C, the boiling reaction was then neutralised with sodium carbonate (approx. 3 g). Water was then removed under reduced pressure. A 90:10 ethanol:water mix (20 mL) was added to the residue and the solution heated to 90° C then filtered. Only starting material was isolated, possibly due to the 4-fluoroaniline contamination mentioned in MD 22-1.

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

Risk and Hazard assessment: Same as Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-1)