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10th September 2012 @ 01:56
Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate for further synthesis into a sulfonamide.

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Reaction start time: 11:30 AM EST 10/9/12
Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1Hpyrrole ( 0.095 g, 0.5 mmol, 1 equiv) and Sulfur trioxide pyridine ( 0.24 g, 1.5 mmol, 3 equiv) were refluxed in toluene (1 mL) for 24 hours. Remaining solvent was decanted. To the remaining solid, water (5 mL) was added and brought to the boil followed by sodium carbonate (5 g). The crude product was concentrated under reduced atmosphere, leaving brown and white solids.

A HNMR and CNMR of the crude product showed that some starting material had been sulfonated at the 3 position while others had been sulfonated at both the 3 and 4 positions on the pyrrole ring. The product was not further purified and instead the reaction was redone on a larger scale.

See also:
Method used from this paper
Repeat Preparation of 1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole (AEW 1-1)
Scale-up (100 mmol) of Paal-Knorr Synthesis of 1-aryl-2,5-dimethyl Pyrrole Core (PMY 1-6)
Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-2)

Risk and Hazard assessment:
MD 6-1 RA
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Attached Files
MD 6-1 Reaction.png
MD 6-1
MD 6-1
MD 6-1 RA
Comments
Re: Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate by Murray Robertson
10th September 2012 @ 02:20
Risk assessment approved - MNR 10/09/12