Phenylboronic Acid → 3-Phenyl-2-thiophenecarboxaldehyde

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3-Bromothiophene-2-carbaldehyde (3 g, 1.67 ml, 14.8 mmol, CAS RN 930-96-1) was dissolved in DME (180 mL) and the resulting solution was evacuated and purged with argon three times. Pd(Ph3P)4 (512 mg, 443 μmol) was added, the reaction flask purged again with argon and stirring was continued at RT for 15 min. Then 2M aqueous Na2CO3 solution was added (14.8 mL, 29.5 mmol) followed by phenylboronic acid (1.98 g, 16.2 mmol). Again the reaction flask was purged with argon and the reaction mixture was heated to 80° C. and stirred for 6.5 h. After evaporation of the solvent, the residue was taken up in Et2O and H2O and the layers were separated. The organic layer was dried over Na2SO4, filtered and evaporated. The crude residue was suspended in CH2Cl2 and n-heptane and the solid was filtered off. The filtrate was evaporated and the crude product purified by flash chromatography on silica gel (gradient EtOAc/n-heptane, 0% to 10%). The product-containing fractions were pooled and further purified by preparative HPLC to give the title compound as a yellow oil (0.939 g, 34%). MS (ESI): m/z=189.2 [M+H]+.

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