Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

Temperature

90 °C

To a solution of 1-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al., US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 90° C. for 40 minutes, cooled to RT and poured into 2.4-L 1 M HCl. After stirring for 30 minutes, the solid was filtered, suspended in EtOH (230 mL) heated to reflux and allowed to cool to RT with stirring overnight. The solid was filtered and washed with 1:1 EtOH hexane (50 mL) to give the title compound. LRMS ESI+ (M+H)+257.0.

1. temperaturecooled to RT
2. filtrationthe solid was filtered
3. temperatureheated
4. temperatureto reflux
5. temperatureto cool to RT
6. stirringwith stirring overnight
7. filtrationThe solid was filtered
8. washwashed with 1:1 EtOH hexane (50 mL)

ORD record

ord-81a2fd2a0bcd4c569ca590260cbcc0e4

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377874B2