5-fluoro-2-iodoaniline NMR

 


                                                                    5-fluoro-2-iodoaniline

NMR Data

1H nmr. CDCl₃. 

4.21 (2H, bs, NH₂), 

6.28 (1H, td, J = 8.5, 2.8), 

6.49 (1H, dd, J = 10.5, 2.8), 

7.57 (1H, dd, 8.7, 6.2)

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 Reference

B. Gabriele, G. Salerno, L. Veltri, M. Costa, C. Massera, Eur. J. Org. Chem. 2001, 4607.

5 -Fluoro-2-iodonitrobenzene (17.4 g; 65.2 mmol) was dissolved in a mixture of ethanol (100 mL) and acetic acid (12 mL) in a large RB flask (at least 500 mL) equipped with an efficient condenser, and the stirred mixture brought to a gentle reflux. Iron powder (26.6 g) was added, followed immediately by iron(III) chloride hexahydrate (3 g). The mixture was refluxed for a further 3 hours, then cooled and filtered using a Buchner funnel (with the help, when necessary, of the addition of ether or ethanol.) To the filtrate was added ether (_{300 mL) and water (}300 mL), and the aqueous layer was repeatedly extracted with ether. The combined organic layers were dried and concentrated, giving 5-fluoro-2-iodoaniline and a pure white solid (14.27 g; 92%).

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