[Babcock_Hall]

We have been trying some test reactions using previously obtained protocols (one from the 1930s), and the preliminary H-1 results from the first protocol is very promising. Today I found the two papers below, which use TFA and a metal-ion salt of nitrate or nitrite.  We are looking for references to other TFA-based methods, just in case our first methods fail.

https://pubs.rsc.org/en/content/articlepdf/1978/p1/p19780001076
S Uemura et al., J Chem Soc Perkin I 1076-1079 1978.
https://jcsp.org.pk/ArticleUpload/1368-6161-1-RV.pdf
Munawar and Khalid 2004
From the first reference:  "A typical procedure is given. To a stirred solution of toluene (0.184 g, 2 mmol) in trifluoroacetic acid (15 ml) was added solid sodium nitrite (0.414g, 6 mmol) in one portion a t 25 "C. The resulted dark brown mixture was stirred for 8 h at 25 "C during which period the mixture turned orange, water (100 ml) was added, and the solution was extracted with benzene (3 x 50 ml)...Reactions with sodium nitrate were carried out similarly."  The substrates in the second reference were haloaromatics, and the conditions were 90 °C.  I don't think that their substrates are similar to ours, and I doubt that I would try this method as is.

[rolnor]

Nice! You can do a lot of chemistry with thiophenes that is not possible with benzenes. If you lithiate thiophene you can alkylate it with alkyl iodides, you dont need to make a cuprate like you need with phenyl lithiums for example.

[Babcock_Hall]

The thiophenes we have tested so far have modest antimicrobial activity.  Our second small-scale nitration using slightly different conditions also went well.  We will combine them to test our purification conditions and to work out any bugs.  We also have a medium-scale nitration reaction waiting in the wings once the first column is completed.