I'm just getting into synthesis, and I seem to be stuck on the first step of a reaction which is simply dissolving 4-Azido-2,3,5,6-tetrafluorobenzoic acid (PFPA-COOH) in dichloromethane (DCM), structure pasted below.
I'm trying to convert the COOH to an NHS ester. The procedure says, "234 mg PFPA-COOH was dissolved in 6.5 mL dry dichloromethane at room temperature". I purchased the PFPA-COOH from TCI Chemicals, and used a bottle of DCM we had in lab. Now, the DCM was not anhydrous and it was not redistilled. I was under the impression that removal of water from the solvent is only used to increase yield since NHS in later steps will react with water. Could this also be the reason I can't seem to dissolve any PFPA-COOH in DCM, or is it possible that I have a bad batch?
Kindly check https://www.researchgate.net/profile/Abdelkader_Bouaziz/post/What_is_the_stability_of_benzyl_azide_as_a_side_chain_in_sulfonated_polyether_sulfones_under_Nucleophilic_polymerization_conditions/attachment/59d61dab79197b80779792a5/AS%3A272163821555713%401441900319190/download/azide-03.pdf
Also check https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2982936/
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