Dimethyl Sulfoxide → HCID 13527237, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-5-methoxybenzaldehyde (21.70 g, 141 mmol) in 280 mL of DMSO were successively added K2CO3 (21.4 g, 1.1 eq.) and ethyl thioglycolate (17.07 mL, 1.1 eq.), and the mixture was vigorously stirred at 50° C. for 5 h. After cooling, the reaction mixture was poured onto crashed ice/HCl, twofold extracted with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated. Flash chromatography (SiO2, hexane/AcOEt=85/15) yielded in the less polar fractions 6.40 g of the title compound as light yellow solid and in the more polar ones 19.27 g of [(2-fluoro-4,5-Dimethoxy-phenyl)-hydroxy-methylsulfanyl]-acetic acid ethyl ester which can be recycled by stirring over night at 70° C. in DMSO in the presence of K2CO3.

Provenance & Evidence