Methyl 2'-hydroxybiphenyl-3-carboxylate synthesis

Yield:92254-28-9 86%

Reaction Conditions:

with thionyl chloride at 0; for 3.17 h;Reflux;

Steps:

Methyl 2'-hydroxybiphenyl-3-carboxylate (4)

Methyl 2'-hydroxybiphenyl-3-carboxylate (4) Thionyl chloride (6.8 mL, 93 mmol) was added at 0°C to a soln of 3 (4.0 g, 18.6 mmol) in MeOH (60 mL). The mixture was stirred for 10 min at 0°C and then heated to reflux for 3 h. Evaporation of the volatiles and aqueous workup (EtOAc, sat. aq. NaHCOs soln; Na₂S0₄) afforded the ester 4 (3.68 g, 86%). Data of 4: Ci₄Hi₂0₃ (228.2). LC-MS (method 2a): R_t = 1 .95 (98), 226.9 ([M-H]-). - NMR (DMSO-de): 9.66 (s, 1 H); 8.16 (t, J = 1 .6, 1 H); 7.89 (d-like m, 1 H); 7.81 (d-like m, 1 H); 7.56 (t, J = 7.7, 1 H); 7.29 (dd, J = 1 .7, 7.6, 1 H); 7.20 (t-like m, 1 H); 6.98 - 6.88 (m, 2 H); 3.87 (s, 3 H).

References:

WO2013/139697,2013,A1 Location in patent:Page/Page column 120