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7th November 2012 @ 05:47
Chlorination of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole using Chlorosulfonic acid to give chlorinated intermediate for sulfonamide formation.


Reaction start time: 6:00 PM EST 7/11/12
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.

Dark brown solid was stuck onto the bottom of reaction vessel, ice (20 mL) was added to the hard solid and shaken until ice had melted. DCM (20 mL) was added and stirred for 2 minutes. The phases were separated and the aqueous layer was washed with DCM (2 × 20 mL). The organic layers were combined and stored overnight in the freezer.

In the morning the light brown solution had turned black, it was concentrated under reduced pressure.

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:
MD 14-1 RA.pdf
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Attached Files
MD 14-1 RA.pdf
MD 14-1.png