Sodium sulfinate SN2 alkylation on sulfur with a triflate

Sodium sulfinate SN2 alkylation on sulfur with a triflate containing electrophilic reagent, how to set up when reagents favor different solvents? I will attach reports of interest. I have a pure sodium sulfinate reagent NaSO2CH2OTBS with 1 alky group already containing a methylene carbon bonded to the sulfur CH2OTBS, and the sulfur or oxygen has the anionic charge with resonance but usually oxygen of course (soft electrophiles favor sulfur reactivity from reports published already in alkylations, and other reports used crown ethers which I tried also already but my issue is finding SM or products in HNMR CDCl3). The electrophile I am using is very activated being an BrCH2CH2OTf but I only want 1 alkylation and no by-product bis-adduct via reaction with the primary bromine adduct from the first desired reaction. Dissolving the sodium sulfinate is problematic when consider DMSO can be problematic for triflate bearing compounds if DMSO acts as an oxygen nucleophile solvolysis. TBAI (can be issue if reacting with the electrophile), crown ethers, low temperature, glovebox, heated 60 degrees due to compound stability in DMF (sodium sulfinate I have) show SM sodium sulfinate decomposes at 80 degrees, and so forth I have tried and analyzed only in CDCl3 but seen no desired product or by-product and if no rxn then the SM would be lost in the aqeuous workup anyway. I use excess electrophile (I do not want my nucleophilic sulfur to have equal chance to react with the desired product is why) 1.5-5 equivalences and add my sodium sulfinate slowly in portions to disfavor bis-byproduct i.e. always favoring excess electrophile over first desired product. Workup is cold water/pH 7.4 phosphate buffer (hydrolysis of electrophile could build acid and I do not want that for TBS group), brine, concentrate - NMR (when using DMF use LiCl to help remove during extractions, and when using DMSO more water washes). What advice on setting up new reactions to screen can you provide or its isolation i.e. reaction conditions, length, was to workup mini to time analyze, and other matters please include. NMR before rxn shows pure SM in deuterated methanol sodium sulfinate and BrCH2CH2OTf in CDCl3 which is made right before setting up the reactions.