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14th April 2013 @ 08:14

Synthesis of the aryl pyrrole core to be synthesised into a sulfonamide.

Reaction start time: 4:00 PM EDST, 12/4/13


This reaction was done in duplicates designated A and B. 4-fluoroaniline (8.8 mL, 93 mmol, 1 equiv.) and 2,5-hexanedione (10 mL, 93 mmol, 1 equiv.) were mixed and heated to 110 °C and left overnight. In the morning, the reaction was cooled to room temperature. The mixture was dissolved in hot EtOH (15 mL) after which a mixture of EtOH (10 mL) and aqueous solution of 10% citric acid (10 mL) was added. Reaction was cooled in an ice bath. The resulting brown crystals were filtered. Black contaminant remainedd in the reaction vessel so the crystals were redissolved in hot EtOH (10 mL) and a solution of 10% citric acid (10 mL) was added and the mixture was cooled with stirring. The resulting brown crystals were filtered and washed with water. Light brown crystals were isolated for reaction A (2.47 g) and reaction B (2.29 g), more crystals still appeared to be in the mother liquor.

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