Sodium Carbonate → 2'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acid

To a solution of 4-carboxybenzeneboronic acid (1.218 g, 7.340 mmol) and Na2CO3 (2.40 g, 22.6 mmol) in water (75 mL) was added p-dioxane (75 mL). This mixture was treated sequentially with 2-iodobenzotrifluoride (1.05 mL, 7.48 mmol) and palladium (II) acetate (151 mg, 0.673 mmol) and allowed to stir at ambient temperature for 16 hours. The solvent was evaporated in vacuo. To the residue was added EtOAc (400 mL) and water (300 mL). The aqueous layer was acidified to pH 1 with 1.0 N aq. HCl and the layers separated. The aqueous layer was extracted with EtOAc (2×200 mL). The organic extracts were combined, washed with brine (200 mL), 5% aq. Na2S2O3 (200 mL), saturated NaCl (200 mL), dried (Na2SO4), and the solvent evaporated in vacuo to afford the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz) d 8.14(2H, d, J=8.1 Hz), ), 7.77(1H, d, J=7.9 Hz), 7.60(1H, t, J=7.5 Hz), 7.52(1H, t, J=7.3 Hz), 7.44(2H, d, J=8.1 Hz) and 7.33(1H, d, J=7.5 Hz) ppm.

1. customThe solvent was evaporated in vacuo
2. additionTo the residue was added EtOAc (400 mL) and water (300 mL)
3. customthe layers separated
4. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
5. washwashed with brine (200 mL), 5% aq. Na2S2O3 (200 mL), saturated NaCl (200 mL)
6. dry with materialdried (Na2SO4)
7. customthe solvent evaporated in vacuo

ORD record

ord-48dda1ac82c742b6ad7a58a5ae116379

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06080870