Hydrochloric Acid → 4'-Methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acid

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Reaction Steps

To a stirred solution of methyl 4′-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate (60 mg, 0.19 mmol) in tetrahydrofuran (3 mL) was added 2.5 M aqueous lithium hydroxide solution (0.77 mL, 1.9 mmol). The mixture was stirred at room temperature overnight, and then acidified to pH=5 by addition of 2N aqueous HCl and extracted with EtOAc (50 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford the title product. 1H NMR (CD3OD, 400 MHz): 8.63 (d, 2H, J=4.8 Hz), 8.16 (t, 1H, J=1.6 Hz), 7.74 (t, 1H, J=2.0 Hz), 7.65 (t, 1H, J=2.0 Hz), 7.56 (d, 2H, J=8.0 Hz), 7.29 (d, 2H, J=8.0 Hz), 7.24 (t, 1H, J=4.8 Hz), 2.39 (s, 3H).

Provenance & Evidence