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3rd September 2012 @ 08:52
4-fluoroaniline (10.4 mL, 110 mmol, 1.1 equiv.) and 2,5-hexanedione (11.7 mL, 100 mmol, 1 equiv.) were heated to 110 °C (oil bath temp.). After 15 hours, reaction was cooled to room temperature. The mixture was dissolved in hot EtOH (15 mL) and a mixture of EtOH (30 mL) and aqueous solution of 10% citric acid (15 mL). The reaction was slowly cooled to approx. 10 °C with periodic shaking. The resulting crystals were filted and washed with water (approx. 200 mL) to obtain the product as a tan crystalline solid containing dark brown solid (16.7 g, 88 mmol) which was found to contain an impurity (NMR 1-1 A). A second pure fraction was obtained as a tan powder from the mother liquors (783 mg, 4.1 mmol, 4.1% yield) NMR 1-1 B. The first crop of crystals were redissolved in hot EtOH (15 mL) and a hot mixture of EtOH (30 mL) and aqueous solution of 10% citric acid (15 mL) was added. The reaction mixture was allowed to cool to room temperature whilst stirring and then gradually cooled to 10 ˚C with periodic swirling. The resulting crystals were filtered and washed with water to obtain the product as tan crystals (16.2 g, 86 mmol, 86% yield). [b]Total yield (16.9 g, 89 mmol, 89% yield) Data[/b] Data in agreement with Paul Ylioja's original synthesis, see below for link [data]3178[/data] [data]3180[/data] [data]3198[/data] [data]3200[/data] [b]References:[/b] [list=1] [*] Manetti, F.; Magnani, M.; Castagnolo, D.; Passalacqua, L.; Botta, M.; Corelli, F.; Saddi, M.; Deidda, D; De Logu, A. [i]ChemMedChem[/i], [b]2006[/b], [i]1[/i], 973–989. doi: [url=http://dx.doi.org/10.1002/cmdc.200600026]10.1002/cmdc.200600026[/url] [/list] [b]Original Experiment:[/b] [blog]223[/blog] [b]Structural Information[/b] InChI=1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 and InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 gives: InChI=1S/C12H12FN/c1-9-3-4-10(2)14(9)12-7-5-11(13)6-8-12/h3-8H,1-2H3 [b]Hazard and Risk Assessment:[/b] [data]3182[/data]
Attached Files
AEW 1-1 A.pdf
AEW 1-1 B.pdf
AEW 1-1.pdf
aew 1-1.png
AEW 1-1 C.pdf
AEW 1-1 D.pdf