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18th December 2012 @ 17:01

Reaction Scheme

4-fluoroaniline (5.2 mL, 55 mmol, 1.1 equiv.) and 2,5-hexanedione (5.85 mL, 50 mmol, 1 equiv.) were heated to 110 °C (oil bath temp.) for 19 hours. The reaction mixture was cooled and dissolved in hot EtOH (25 mL) and aqueous citric acid (10% w/v, 7.5ml). The solution was slowly cooled with occasional shaking to 10°C, whereupon tan and dark precipitates formed. The solution was filtered and washed with cold EtOH (10 mL) and water (200 mL), whereupon further tan precipitate formed in the filter flask. This filtrate was re-filtered, and the combined precipitates were washed with water (200 mL) to give a tacky brown solid (11.14 g, >99% yield, NMR PT-1-1-A). The solid was dissolved in DCM (100 mL) and washed with aqueous citric acid (5% w/v, 100 mL) dried over magnesium sulfate, then filtered and concentrated in vacuoto give a brown solid (8.571 g, 90.5% yield, NMR PT-1-1-B).

DataData in agreement with Paul Ylioja's and Alice Williamson's original reactions (see below for links)

PT-1-1-A.pdf
PT-1-1-B.pdf

References:

 

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Attached Files
PT-1-1 scheme.png
PT-1-1 Risk Assessment.pdf
PT-1-1-A.pdf
PT-1-1-B.pdf
Comments
Re: Repeat Preparation of 1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole (PT 1-1) by Patrick Thomson
18th December 2012 @ 17:07
Scaled it down by 50% due to material availability.