Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

Participants

Reaction Conditions

Reaction Steps

Acrylic acid (9.61 g, 133 mmol), TEA (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol) were added to a solution of 1-bromo-4-iodo-2-methoxybenzene (US 2004/0254159) (33.45 g, 107 mmol) in MeCN (100 mL). The reaction mixture was heated to 90° C. for 40 min, cooled to RT and poured into 2.4 L 1M HCl. After stirring for 30 min, the solid was filtered, heated to reflux in EtOH (230 mL), allowed to cool to RT and stirred overnight. The solid was filtered and washed with 1:1 EtOH:hexanes (50 mL) to give desired product. LRMS ESI+ (M+H)+ 257.0.

Provenance & Evidence