Sodium Hydroxide → HCID 39834387, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodoanisole (0.6 mL, 5 mmol), 1-methyl-2-(tributylstannyl)-1H-imidazole (Bull. Chem. Soc. Jpn. 1986, 59, 677, 2.5 g, 6 mmol), and dichlorobis(triphenylphosphine)palladoim(II) (421 mg, 0.6 mmol) in N,N-dimethylformamide (10 mL) was stirred at 60° C. for 8 h under nitrogen atmosphere. The reaction mixture was poured into 2 N sodium hydroxide aqueous solution (10 mL) and the basic mixture was extracted with ethyl acetate (30 mL×6). The combined organic extracts were washed with brine (10 mL×2) and dried (sodium sulfate). After removal of solvent, the residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20/1) to afford 724 mg (77%) of the title compound as pale orange oil: 1H-NMR (CDCl3) δ 7.39–7.33 (1H, m), 7.22–7.16 (2H, m), 7.13–7.12 (1H, m), 6.97–6.94 (2H, m), 3.86 (3H, s), 3.76 (3H, s); MS (ESI) m/z 189 (M+H)+.

Provenance & Evidence