Ammonium Chloride → HCID 58669199, compound

Participants

Reaction Steps

5-bromo-3-methyl-4-cyclohexyl-2-formylthiophene (1.5 g, 5.2 mmol), 3-methyl-4-cyclohexylthiophene-2-boryl pinacolate (1.9 g, 6.24 mmol) and Bu4NBr (33 mg, 0.1 mmol) were added to a 100 ml flask. The mixture of solids was evacuated for 2 hours, then dissolved in dry toluene (30 ml) under argon with stirring. Tetrakis(triphenylphosphine)palladium (100 mg, 0.09 mmol) was added and the solution was heated to 95° for 16 hours. Afterwards, an additional aliquot of boronate (0.5 g) and tetrakis(triphenylphosphine)palladium (50 mg) were added. The reaction was checked, after stirring an additional 20 hours, and found to be complete. The mixture was poured into a saturated solution of ammonium chloride, and extracted with toluene (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4. After the solvent was removed by rotary evaporation. The remaining oil was purified by column chromatography (CH2Cl2:petroleum ether, 2:3) to afford the product 2-formyl-3-methyl-4-cyclohexylthiophene dimer as a yellow solid (1.5 g, 75%). 1H NMR (CDCl3) δ 10.08 (s, 1, CHO), 7.01 (s, 1,thienyl-H), 2.67 (m,1,cyclohexyl methane), 2.65 (s, 3,CH3), 2.52 (m,1,cyclohexyl methane), 2.07 (s, 3,CH3), 1.78 and 1.31 (m, 20, cyclohexyl). 13C NMR (CDCl3) δ 182.5, 148.3, 147.9, 146.5, 140.4, 138.2, 136.7, 128.6, 119.4, 39.7, 38.8, 33.8, 31.3, 27.1, 26.9, 26.3, 25.9, 14.01, 13.3.

Provenance & Evidence