To enable divergent access to the aryl OSF reagents for deFS or SuFEx processes, we targeted phenol sulfide 131 as a strategic point for diversification (Scheme 6a). To access this material on multi gram scale, we initially re-developed the thiol alkylation. Employing an FeCl3 catalyst (10 mol%), generated sulfide 2b in good yield and was scaled up to 14 mmol/6.0 g (see SI for further discussion). The TIPS group was readily removed to generate the diversifiable intermediate 131 as a bench stable white solid, which was stable to storage at room temperature for >6 months.From here, the phenol was effectively alkylated with benzyl bromide in quantitative yield by using K2CO3 in acetone. The oxidation elimination/fluorination process afforded benzyl OSF 132. Applying 3-fluorobenzyl bromide gave the corresponding OSF reagent (133), which was reacted with H-Ala-NH2 hydrochloride to generate an oxetane analogue of the drug safinamide which contains a benzylamine (141, Scheme 6b, see SI for X-Ray crystal structure).