p-Anisoyl chloride → HCID 10808337, compound

Participants

Reaction Steps

The known compound, 2-benzyl-benzo[b]thiophene (CA reg. no. 3407-15-6) was acylated with one equivalent of anisoyl chloride using one equivalent of a tin (IV) chloride promoter in carbon disulfide solvent to afford (2-benzyl-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone (85% yield). This compound was demethylated using six equivalents of pyridinium hydrocholide at 228° C. to afford (2-benzyl-benzo[b]thiophen-3-yl)-(4-hydroxy-phenyl)-methanone (90% yield). This compound was brominated according to the procedure in Example 4 to afford the title compound as a white solid (95% yield): mp 155.5-156.5; MS m/e 500 (M)+; Analysis for: C22H14Br2O2S Calc'd: C, 52.61; H, 2.80 Found: C, 52.43; H, 2.71

Provenance & Evidence