反应详情

Iodomethane (0.383 mL, 6.16.mmol) was added to a stirred suspension of 2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol (2.13 g, 4.4 mmol), potassium carbobnate (0.669 g, 4.34 mmol) and DMF (15 mL) at room temperature under a dry nitrogen atmosphere. After 3 h, the reaction mixture was diluted with water and the resulting solid was filtered and washed with water. The solid was taken up in dichloromethane and silica gel (40 mL) was added. The solvent was removed and the adsorbate was flash chromatographed (90:10 petroleum ether:dichloromethane) to provide the title compound as a white solid (2.0 g, 91%): mp 238.5-239.5° C.: NMR (CDCl3); δ 8.36 (ddd, J=8, 1, 1 Hz, 1H), 7.84 (ddd, J=8, 1, 1 Hz, 1H), 7.67 (ddd, J=8, 7, 1 Hz, 1H), 7.60 (s, 2H), 7.58 (ddd, J=8, 1, 1 Hz, 1H), 7.50 (ddd, J=8, 7, 1 Hz, 1H), 7.45 (ddd, J=8, 7, 1 Hz, 1H), 7.20 (ddd, J=8, 7, 1 Hz, 1H), 6.80 (ddd, J=8, 1, 1 Hz, 1H), 4.11 (s, 3H, CH3); MS (EI): [M+], 3 bromine isotope pattern, 574 (35%), 576 (95%) 578 (100%) 580 (45%); Anal. Calc. for C23H13Br3OS: C, 47.87, H, 2.27, N, 0.00. Found: C, 47.73, H, 1.88, N, 0.03.

1. customat room temperature
2. filtrationthe resulting solid was filtered
3. washwashed with water
4. additionsilica gel (40 mL) was added
5. customThe solvent was removed
6. customchromatographed (90:10 petroleum ether:dichloromethane)