(1,1'-Biphenyl)-3-carboxylic acid → HCID 86088856, compound

Participants

Reaction Steps

Oxalyl chloride (132 μL, 1.5 mmol) was added over a 10 minute period to a mixture of 3-phenylbenzoic acid (200 mg, 1 mmol) dissolved in a mixture THF/DMF (3.5 mL/58 μL). After the addition, the reaction was stirred at room temperature for 2.5 hours. Sec-butylamine (253 μL, 2.5 mmol) was then added into half of the acid chloride solution at 0° C. The reaction was then stirred at room temperature for 18 hours. The reaction was concentrated and water was added to the residue. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic layers were washed with 2N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. Diethyl ether was added to the residue and a white solid precipitated. It was collected by filtration and rinsed with a small amount of diethyl ether. The white solid was then dried under vacuum (89 mg, 70%). NMR 1H (ppm, CDCl3): 7.95 (s, 1H), 7.68 (d, J3=7.51 Hz, 2H), 7.59 (d, J3=7.63 Hz, 2H), 7.50-7.33 (m, 4H), 5.97 (br. s., 1H), 4.30 (hept., J3=6.86 Hz, 1H), 1.58 (quint., J3=7.26 Hz, 1H), 1.23 (d, J3=6.56 Hz, 3H), 0.97 (t, J3=7.36 Hz, 3H).

Provenance & Evidence