Besides, alkylsilanes are not very resistant against strong acids.
I have definitely observed some desylilation depending on acid/temperature, but I did not think the alkylsilane group would be the main issue as the reaction seems to work for making siliconrhodamines:
A general approach to spirolactonized Sirhodamines, Chem. Commun., 2014,50, 14374-14377 https://pubs.rsc.org/en/content/articlelanding/2014/cc/c4cc06178k#!divAbstract
Additionally, the acid-catalyzed method doesn't work either for making carbofluorescein (Si replaced by C).
Why don’t you try a classical, Lewis acid catalyzed Fries rearrangement of the corresponding diphenol diester and try to obtain the desired regioselectivity by temperature control?
In Fries rearangement, the reaction and substituent orientation mechanisms are somehow different than the Friedel-Crafts ones.
If you halogenate the p-position you can use Pd-chemistry to get the acyl-derivative.
Thanks, these are good suggestion for mono-acylation, however making siliconfluorescein requires a double reaction with both aromatic rings, so I'm not sure that the second step would proceed with these methods? I'm unfamiliar with the Fries.
The current best synthetic approach to siliconfluorescein/rhodamines involves di-bromination and lithiation before reacting with anhydride derivatives:
General Synthetic Method for Si-Fluoresceins and Si-Rhodamines, ACS Cent. Sci. 2017, 3, 9, 975-985https://pubs.acs.org/doi/full/10.1021/acscentsci.7b00247
However this approach limits the nature of functionalizable groups that can be introduced easily, which is why I'm looking for alternative strategies.