3-Amino-1,1'-biphenyl-4-carboxylicacid

20776-50-5

98-80-6

4445-43-6

Pd(PPh3)4 (0.052 g, 0.045 mmol) was added to degassed DMF (10 mL) and 1 M K2CO3 aqueous solution (7 mL) under nitrogen protection using 2-amino-4-bromobenzoic acid (0.992 g, 4.46 mmol) and phenylboronic acid (0.832 g, 6.69 mmol). The reaction mixture was stirred at 80 °C for 16 hours. Upon completion of the reaction, DMF was removed under reduced pressure.The residue was dissolved in 4 N NaOH aqueous solution (40 mL) and the aqueous phase was washed twice with ethyl acetate (2 x 50 mL). The pH of the aqueous phase was adjusted to 5 by the addition of 4 N HCl. Subsequently, the aqueous phase was extracted three times with ethyl acetate (3 x 50 mL) and once with DCM-MeOH (9:1, 50 mL). All organic phases were combined, dried with MgSO4, and the solvent was evaporated under reduced pressure to give a beige solid. The solid was ground in ether, filtered and dried to give 3-amino-[1,1'-biphenyl]-4-carboxylic acid as a beige solid (0.721 g, 76% yield). mS (ESI, m/z): 214.3 [M + H+] C13H11NO2; tR = 0.78 min.