Water → HCID 86755714, compound

Participants

Reaction Steps

To a suspension 3-(6-bromo-benzo[b]naphtho[2,3-d]thiophen- 11-yl)-2,6 difluoro-phenol (0.200 g, 0.453 mmol) and potassium carbonate (0.085, 0.612 mmol) in N,N-dimethylformamide (2 mL) was added methyl bromoacetate (0.086 mL, 0.906 mmol) dropwise at room temperature under a dry nitrogen atmosphere. After stirring 2.5 hours the reaction mixture was combined with water (50 mL) and the organics were extracted with ether. The extract was combined with silica gel, the solvent was removed and the adsorbate was flash chromatographed (90/10 petroleum ether/ethyl acetate). The solvents were chased with benzene (2×) and petroleum ether to give [3-(6-bromo-benzo[b]naphtho[2, 3-d]thiophen-11-yl)-2, 6-difluoro-phenoxy]-acetic acid, methyl ester as a white solid (0.198 g, 85%). To a solution of this methyl ester (0.190 g, 0.370 mmol) in tetrahydrofuran (3 mL) and methanol (1 mL) was added a 1 N aqueous solution of potassium hydroxide (0.55 mL, 0.55 mmol) dropwise at room temperature. After stirring 1 hour the solvents were removed and water was added to the solid residue. The aqueous mixture was acidified with 10% HCl and the organics were extracted with ether. After several minutes of vigorous shaking the layers were separated and the organic layer was washed with water and concentrated. The residue was chased with benzene and dried in vacuo to give the title compound as a white solid (0.177g, 95%): mp 195-197° C.: NMR (400 MHz, DMSO-d6): 8 13.11 (broad s, 1 H), 8.31 (d, J=8 Hz, 1 H), 8.09 (d, J=8 Hz, 1 H), 7.83-7.79 (m, 1 H), 7.64-7.46 (m, 4 H), 7.31-7.27 (m, 1 H), 7.23-7.17 (m, 1 H), 6.81 (d, J=8 Hz, 1 H), 4.89 (s, 2 H); MS(-FAB): (M-H): one bromine pattern observed: 497/499 (35%138%); HRMS: Calc. for C24H13BrF2O3S M+: 497.97368, measured mass: 497.97787, mass deviation 4.19 mmu; Anal. HPLC 97% pure; Anal. Calc. for C24H13BrF203S: C, 57.72, H, 2.62% N, 0.00. Found: C, 56.77, H, 2.79% N, 0.00.

Provenance & Evidence