Citric Acid → HCID 68957343, compound

Participants

Reaction Conditions

Reaction Steps

To N,N-dimethylacetamide 2.0 mL solution of tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate 0.10 g were added 3-bromo-o-xylene 0.064 mL, tributylamine 0.15 mL, palladium acetate 4.0 mg and tri-tert-butylphosphine tetrafluoroborate 3.0 mg at room temperature, and it was stirred under nitrogen atmosphere at 120° C. for 2 hours. Palladium acetate 4.0 mg and tri-tert-butylphosphine tetrafluoroborate 3.0 mg were added to it, and it was stirred under nitrogen atmosphere at 120° C. for 2 hours. 3-Bromo-o-xylene 0.064 mL, tributylamine 0.11 mL, palladium acetate 4.0 mg and tri-tert-butylphosphine tetrafluoroborate 3.0 mg were added to it, and it was stirred under nitrogen atmosphere at 120° C. for 5 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-((E)-2-(2,3-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoate.

Provenance & Evidence