Synthesis
General procedure for the synthesis of 2-(3-bromophenyl)-2-methylpropionic acid from methyl 2-(3-bromophenyl)-2-methylpropionate: Sodium hydroxide solution (2M, 20 mL) was added to a mixture of methanol (20 mL) and tetrahydrofuran (20 mL) of methyl 2-(3-bromophenyl)-2-methylpropionate (6.5 g). The reaction mixture was heated to reflux for 2 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was partitioned between water (100 mL) and dichloromethane (100 mL). The aqueous phase was acidified with 2 M hydrochloric acid and extracted twice with dichloromethane (100 mL and 50 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent to afford the target compound 2-(3-bromophenyl)-2-methylpropionic acid (4.55 g, two-step yield 68%) as a milky white solid. NMR hydrogen spectrum (CDCl3) data: δH 7.54 (s, 1H), 7.40 (d, 1H), 7.33 (d, 1H), 7.21 (t, 1H), 1.59 (s, 6H).
References
[1] Patent: WO2010/52448, 2010, A2. Location in patent: Page/Page column 37
[2] Patent: WO2004/48374, 2004, A1. Location in patent: Page 47
