1,4-Bis(bromomethyl)benzene → 5-(4-Bromomethylbenzyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

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Reaction Steps

A solution of the title B compound in Example 9, 2,4-dimethoxybenzyl-1,1-dioxo-1,2,5-thiadiazolidin-3-one (2.0 g, 6.98 mmol) in CH2Cl2 (100 mL) is treated with DBU (1.06 g, 6.98 mmol). α, α′-Dibromo-p-xylene (9.2 g, 34.9 mmol) is added and the mixture is stirred at RT for 16 h. The mixture is filtered and the filtrate is concentrated to 20 mL. The mixture is chromatographed on silica gel using CH2Cl2 as the eluent. The residual α, α′-dibromo-p-xylene is removed from the product by triturating with Et2O to afford 5-(4-bromomethyl-benzyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a white solid: [M+H]+=469.

Provenance & Evidence