Cesium fluoride → Methyl 4-(2,4-difluorophenyl)benzoate

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Reaction Conditions

Reaction Steps

Dissolve 2,4-difluoro-1-iodo-benzene (0.25 mL, 2.08 mmol) in anhydrous 1,2-dimethoxyethane (30 mL). Add 4-methoxycarbonyl-phenyl-boronic acid (0.375 g, 2.08 mmol), cesium fluoride (1.58 g, 10.42 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.170 g, 0.208 mmol). Degas the mixture thrice and back-fill with nitrogen. Immerse the mixture into a pre-heated (85° C.) oil bath and stir overnight. Filter the hot mixture through Celite® and concentrate in vacuo. Subject the residue to silica gel flash column chromatography (40 g column, 0-10% ethyl acetate/n-hexane) to yield the desired product (0.441 g, 85%). mass spectrum (n/e): 249.0 (M+1).

Provenance & Evidence