Dimethylformamide → HCID 54352918, compound

Participants

Reaction Steps

4-(Benzo[b]naphtho[2,3-d]thiophen-11-yl)-2,6-diiodo-phenol (0.543 g, 0.94 mmol), methyl bromoacetate (0.181 mL, 1.88 mmol), potassium carbonate (0.141 g, 1.03 mmol) and N,N-dimethylformamide (5.4 mL) were combined and stirred at ambient temperature for 1 h. The reaction mixture was added to water and filtered. The solid was washed with water and dried in vacuo to provide the (4-benzo [b]naphtho[2,3-d]thiophen-11-yl-2,6-diiodo-phenoxy)-acetic acid methyl ester as a white solid (0.537 g, 88%): mp 203-205 ° C. Aqueous potassium hydroxide (0.5 N, 2.54 mL, 1.28 mmol) was added to a stirred solution of this methyl ester (0.55 g, 0.85 mmol) in THF (5.0 mL) at ambient temperature. After 1 h the solution was concentrated, diluted with water (75 mL) and acidified with 10% aqueous HCl. The solid was filtered and washed with water to provide the title compounds as a white solid (0.428 g, 80%): mp 250-252° C.: NMR (DMSO-d6); δ8.66 (s, 1 H), 8.07 (d, J=8 Hz, 1 H), 8.01 (d, J=8 Hz, 1 H), 7.93 (s, 2 H), 7.61 (ddd, J=8, 7, 1 Hz, 1 H), 7.54-7.48 (m, 2 H), 7.47 (ddd, J=8, 7, 1 Hz, 1 H), 7.27 (ddd, J=8, 7, 1 Hz, 1 H), 6.71 (d, J=8 Hz, 1 H), 4.69 (s, 2 H); MS (EI): 636 (100%, MI); Anal. Calc. for C24H14I2O3S: C, 45.31, H, 2.22, N, 0.00. Found: C, 44.95, H, 1.99, N, 0.23.

Provenance & Evidence