Reaction Steps
2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen- 11 -yl)-phenol (1.0 g, 1.78 mmol), methyl bromoacetate (0.35 mL, 3.70 mmol), potassium carbonate (0.50 g, 3.62 mmol) and N,N-dimethylformamide (5 mL) were combined and stirred at ambient temperatures overnight. The reaction mixture was added to water and filtered. The solid was washed with water and dried in vacuo to provide the title compound as a white solid (1.11 g, 98%): mp 183-184° C.: NMR (CDCl3); δ8.36 (ddd, J=8, 1, 1 Hz, 1 H), 7.84 (ddd, J=8, 1, 1 Hz, 1 H), 7.68 (ddd, J=8, 7, 1 Hz, 1 H), 7.62 (s, 2 H), 7.57 (ddd, J=8, 1, 1 Hz, 1 H), 7.51 (ddd, J=8, 7, 1 Hz, 1 H), 7.42 (ddd, J=8, 7, 1 Hz, 1 H), 7.18 (ddd, J=8, 7, 1 Hz, 1 H), 6.72 (ddd, J=8, 1, 1 Hz, 1 H), 4.88 (s, 2 H), 3.94 (s, 3 H); MS (EI): [M+], 3 bromine isotope pattern, 632 (30%), 634 (90%) 636 (100%) 638 (35%); Anal. Calc. for C25H15Br3O3S: C, 47.27, H, 2.38, N, 0.00. Found: C, 47.17, H, 2.19, N, 0.09.
