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15th November 2012 @ 05:17
Chlorination of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole using Chlorosulfonic acid as an intermediate for sulfonamide synthesis.

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Reaction start time: 4:15 PM EST 8/11/12

Solid AEW 1-1 (275 mg, 1.45 mmol, 1 equiv.) was mixed under an inert atmosphere. Chlorosulfonic acid (100 µL, 1.5 mmol, 1 equiv.) was added and the reaction was heated to 60 °C for one and a half hours. Ice (20 mL) and DCM (20 mL) were added to the black solid and swirled till it had dissolved. The phases were separated and the aqueous layer was washed with DCM (2 × 20 mL). The aqueous layer turned red indicating unknown product was dissolving in the aqueous layer.

See also:
Repeat Preparation of 1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole (AEW 1-1)
Chlorosulfonation of aryl pyrrole PMY 1-6 (PMY 54-1)

Risk and Hazard assessment:
Same as MD 14-1 Chlorination of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (MD 14-1)
Comments
Re: Chlorination of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (MD 14-2) by Patrick Thomson
13th December 2012 @ 12:00
What's the status of this molecule and the other sulfonamide links? I have a small amount of time I could give and this looked interesting as we're playing with chlorosulfonation for sulfonamide elaboration here just now.