I want to hydrolyse a phosphonic acid diethylester to the corresponding free phosphonic acid. In the literature, it is described, that usually strongly basic or acidic conditions are utilized to achieve this.
The Hydrolysis of Phosphinates and Phosphonates: A Review. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8150351/
Alternatively one can utilize ester cleavage by TMSBr and water workup.
In my case, however, multiple complications occur. R is a complex substituent, which will not tolerate too acidic conditions. In addition, when performing a reaction under basic conditions, the problem is, that base like NaOH or KOH would introduce a very polar species to the mixture in which the product can not separated off easyly from the free phosphonic acid that would be for sure also very polar. (I know, that one possible way get rid of the excess would be the utilization of ion exchange, but from my experience this is an extremely time consuming process when your product as well your impurities are UV inactive.) In addition to that, reaction control would be problematic due to the fact, that the product is likely to co-elute with the base, therefore the reliable reaction control by LCMS, would be problematic, also because the product is not carrying UV active groups. I am therefore wondering if there are possible other strategies to transform the diester into the acid preferably in a fashion, that does not create a problematic purification situation and work in comparison to TMSBr with milder conditions that are not too acidic.