4-Fluorostyrene → Methyl 2-[2-(4-fluorophenyl)ethenyl]-5-methoxybenzoate

Participants

Reaction Steps

A mixture of methyl 2-bromo-5-methoxybenzoate (28.3 g, 115 mmol), 4-fluorostyrene (20.6 ml, 173.3 mmol), tert-n-butylamine (2.7 ml, 11.5 mmol), Pd[(o-tolyl)3 P]2 Cl2 (0.9 g, 1.15 mmol), and NaHCO3 (14.6 g, 173.3 mmol), and water (220 ml) was stirred and heated at reflux for 16 hours. The reaction mixture was diluted with water (200 ml) and extracted with ethyl acetate (2×400 ml). The extracts were washed with 2M HCl (100 ml), water (100 ml), brine (100 ml), dried (MgSO4), filtered and evaporated to dryness. The brown gum obtained was purified by chromatography on silica (90 g, Biotage column), eluting with a gradient of ethyl acetate in iso-hexane (0%-20% ethyl acetate). The relevant fractions were combined and evaporated to give methyl 2-[2-(4-fluorophenyl)ethenyl]-5-methoxybenzoate, (43.5 g)

Provenance & Evidence