Acetic Acid → 2-(4-bromophenyl)-1H-imidazole

関与物質

反応手順

To a solution of 4-bromobenzonitrile (80.0 g, 440 mmol) in MeOH (800 mL) was added NaOMe (20.1 mL, 87.9 mmol). The mixture was allowed to stir at ambient temperature for 5.5 hours. 2,2-Dimethoxyethanamine (61.6 mL, 571 mmol) was added followed by acetic acid (50.3 mL, 879 mmol). The reaction mixture was heated to 50° C. for 1 hour and then cooled to ambient temperature. MeOH (200 mL) and HCl (200 mL, 1200 mmol) were added, and the reaction mixture was heated to 65° C. for 18 hours. The reaction mixture was then concentrated, and washed with 1:1 H2O:Et2O (2000 mL). The pH of the aqueous layer was adjusted to pH=9 with 6 N NaOH. The resulting solid was filtered and dried to give 2-(4-bromophenyl)-1H-imidazole (20.0 g, 20%). LCMS (APCI+) m/z 223, 224 [M+H]+.

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