4-(Bromomethyl)benzoic acid → HCID 67138314, compound

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Reaction Steps

To a suspension of the title B compound in Example 9, 2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (13.87 g, 48.4 mmol) and 4-bromomethylbenzoic acid (10.42 g, 48.4 mmol) in CH2Cl2 (150 mL) is added DBU (14.5 mL, 96.9 mmol) at once and the mixture is stirred at RT overnight. The reaction mixture is washed two times with 1N aqueous HCl, one time with brine, then dried over anhydrous MgSO4 and concentrated to a small volume to crystallize the product. The solid is collected by filtration, washed with ethyl ether and dried under high vacuum to afford 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid: mp=175-177° C.; [M−1]−=419.

Provenance & Evidence