反应详情

A mixture of 9H-carbazole (5.51 g, 33 mmol, available from Aldrich, Milwaukee, Wis.), 4-iodoanisole (10 g, 43 mmol, available from Aldrich), powdered potassium carbonate (36.43 g, 264 mmol), copper powder (8.38 g, 132 mmol) and 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane, 0.56 g, 2.1 mmol, obtained from Aldrich) was refluxed in o-dichlorobenzene (30 ml, obtained from Aldrich) under nitrogen for 24 hours. The copper and inorganic salts were filtered. The solvent was removed by distillation. The product, 9-(4-methoxyphenyl)carbazole, was recrystallized, washed with methanol, filtered, and dried. The yield was 8.432 g (93.7%). The 1H-NMR spectrum (300 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 4.04 (s, 3H, OCH3), 7.24-7.63 (m, 8H, Ar.), 8.35-8.40 (m, 4H, Ar.). The 13C-NMR spectrum (75.4 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 55.95 (OCH3), 110.07, 115.44, 120.03, 120.68, 123.53, 126.25, 128.90, 130.65, 141.78, 159.26 (all Ar). The infrared absorption spectrum of the product was characterized by the following the following absorption frequencies (KBr windows, in cm−1): 3040 (C—H Ar), 2900 (C—H Alk), 1250 (C—O—C). The mass spectrum of the product was characterized by the following ions (in m/z): 274 (M+).

1. filtrationThe copper and inorganic salts were filtered
2. customThe solvent was removed by distillation
3. customThe product, 9-(4-methoxyphenyl)carbazole, was recrystallized
4. washwashed with methanol
5. filtrationfiltered
6. customdried
7. customThe infrared absorption spectrum of the product
8. customthe following absorption frequencies (KBr windows, in cm−1)