DraconicAcid
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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?
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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Hendrik
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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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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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I have sodium fluoride, and that's it. I can make HF in situ from that.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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myr
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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).
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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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Yeah, I can order stuff, but we have a limited budget.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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