Potassium Carbonate → 3-(3-Methoxy-5-nitro-phenyl)-thiophene

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-iodo-3-methoxy-5-nitro-benzene (1.0 g, 3.59 mmol) in ethanol (18 mL) in a microwave tube were added tetrakis(triphenylphosphine)palladium(0) (837 mg, 0.72 mmol), thiophen-3-ylboronic acid (748 mg, 5.55 mmol), and potassium carbonate (496 mg, 3.58 mmol) at room temperature. The mixture was heated to 160° C. under closed microwave conditions for 30 minutes. After cooling to room temperature, the colored mixture was filtered and the filter cake was washed with water. The filtrate was diluted with 1.0 N HCl and the organic compound was extracted into ethyl acetate (2×50 mL). The combined organic extracts were washed with brine solution (100 mL) and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by using an ISCO 80 g column, eluting with 0-10% ethyl acetate in hexanes to obtain 3-(3-methoxy-5-nitro-phenyl)-thiophene (776 mg, 92%) as a light yellow oil: EI(+)-HRMS m/e calculated for C11H9NO3S (M+)+ 235.0303, found 235.0298.

Provenance & Evidence