Carbazole → HCID 57983707, compound

Participants

Reaction Conditions

Reaction Steps

To a three neck round bottom flask, was charged bromo-3,5-dimethoxybenzene (1.54 g, 7.1 mmol), carbazole (1.186 g, 7.1 mmol), potassium phosphate (3 g, 14.2 mmol) and copper iodide (0.14 g, 0.7 mmol). Dioxane (40 ml) was added and the reaction flask. The flask was evacuated and flushed with argon. Dimethylethylene diamine (0.14 g, 1.6 mmol) was then added to the reaction flask under a strong purge of argon. The reaction mixture was then heated at 95° C. for 48 h under argon. The reaction was followed by TLC. After the reaction was complete, the solution was cooled down to room temperature, and 10 mL of H2O was added. The reaction mixture was extracted with methylene chloride and the organic and aqueous phases were separated. The organic phase was further washed twice with 100 mL of water (×2) and once with 100 mL of brine (×1) and dried over Na2SO4. After solvent removal under vacuo, afforded crude product. Crude product was dissolved in CH2Cl2 and hexanes were added until the colored residues precipitated out. The solution was filtered to remove the colored residues. The mother liquor was concentrated to afford 1.0 g (46.5%) of light yellow oil as the product. 1H NMR (CDCl3) δ 7.98 (d, 2H), 7.35 (d, 2H), 7.23 (d, 2H), 7.11 (t, 2H), 6.6 (s, 2H), 6.43 (s, 1H), 3.65 (s, 6H). EI-MS: 303(M+).

Provenance & Evidence