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Author: Subject: Simple organofluorines?
DraconicAcid
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[*] posted on 6-8-2018 at 15:11
Simple organofluorines?


I don't have much access to fluorine-containing compounds, but if my cards are played properly, I may have access to an NMR spectrometer in the next year or two. I'd like to make a few simple fluorine-containing compounds so that I can show my students fluorine coupling (sadly, it won't be able to to 19F NMR, or I'd be making as many transition metal fluoride complexes as I could). Any suggestions?



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Hendrik
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[*] posted on 6-8-2018 at 18:14


What fluorine source do you own? Hydrofluoric acid? If so, why not try synthesizing some simple fluorocarbons? If you happen to be able to get some CCl2F2 (it was used as a refrigerant, but it was replaced with other less ozone depleting fluorocarbons), you could make some CF4 using HF.
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clearly_not_atara
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[*] posted on 6-8-2018 at 18:15


5-fluorouracil comes to mind. Typically made by electrophilic fluorination of uracil; don't make the fluorination reagent yourself (duh).





[Edited on 04-20-1969 by clearly_not_atara]
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DraconicAcid
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[*] posted on 7-8-2018 at 08:23


I have sodium fluoride, and that's it. I can make HF in situ from that.



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myr
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[*] posted on 7-8-2018 at 09:00


I hope this can be useful. My original idea was addition of HF across an alkene, but this is impossible b/c of the strong H-F bond. I found this, instead- which uses a HF-Pyridine complex which could be made from NaF I guess.


DOI:10.1055/s-0029-1220011
Quote:
General/Typical Procedure: Halofluorination of Alkenes with HF·Py/TBCA System; General Procedure. A magnetically stirred mixture of the alkene (2 mmol) and 70% HF·Py (4 mmol) in anhyd CH2Cl2 (10 mL) contained in a 50 mL, single-necked PTFE flask equipped with a septum and under argon, was treated with trihaloisocyanuric acid (0.68 mmol) at 0 °C. After the addition, the ice bath was removed, and the stirring continued at r.t. After completion, the reaction was quenched with distilled H2O (10 mL), and the product was extracted with CH2Cl2 (3 × 10 mL). The combined organic layers were subsequently washed with sat. aq NaHCO3 (10 mL) and dried (Na2SO4). After filtration and evaporation of the solvent, the product was characterized by standard analytical techniques. 2-Bromo-1-fluoro-1-phenylethane, Conv.: 100%, Colorless liquid, Time: 20 min, Ratio styrene-HF·Py-TBCA: 1:10:0.34. 1H NMR (200 MHz, CDCl3): δ = 3.5-3.7 (m, 2 H), 5.5-5.8 (ddd, J = 46.9, 7.0, 4.6 Hz, 1 H), 7.4 (m, 5 H). 13C NMR (50 MHz, CDCl3): δ = 34.4 (CH2, d, J = 28.4 Hz), 92.8 (CH, d, J = 178.0 Hz), 125.8 (2 CH, d, J = 6.8 Hz), 128.8 (2 CH, s), 129.3 (CH, s), 137.2 (C, d, J = 20.3 Hz). 19F NMR (282 MHz, CDCl3): δ = -174.7 (m). MS: m/z (%) = 202 and 204 [M+ and (M + 2)+, 7], 122 (3), 109 (100), 103 (8), 77 (11), 51 (14).


Also, F- should open up an epoxide ring I think rather easily. This was my first result: https://www.sciencedirect.com/science/article/pii/S002211399...

Does not your college have access to Sigma-Aldrich and similar companies? You could order small amounts of a more feasible fluorinating agent.
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DraconicAcid
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[*] posted on 7-8-2018 at 10:29


Yeah, I can order stuff, but we have a limited budget.



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