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31st January 2013 @ 17:10

Reaction scheme MD 22-1"

 

 

Reaction start time: 5:00 PM EST 21/1/13
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 contained contaminated black crystals. The crystals were re-dissolved in hot EtOH (10 mL) and a mixture of EtOH (10 mL) and aqueous solution of 10% citric acid (10 mL) were added and the mixture cooled. The resulting crystals were filtered and washed with water. Black contaminate (thought to be 4-fluoroaniline) still remained, product was used in next reaction without further purification.

See also:Synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through ester synthesis (MD 17-1)

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

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MD 22-1.png
Scheme
Scheme