Table 3. General Pathway for the Synthesis of 6-(2-Bromo-3-(bromomethyl)phenyl)-2,3-dihydrobenzo[b][1,4]dioxine (1g), 1,1′:2′,1″-Terphenyl (1b), 6-(3-(Bromomethyl)-2-fluorophenyl)-2,3-dihydrobenzo[b][1,4]dioxine (1d), [1,1′:2′,1″-Terphenyl]-3′-ylmethanol, 2-Bromo-3-(bromomethyl)-3′-fluoro-1,1′-biphenyl (1f), and 2′-Bromo-3′-(bromomethyl)-[1,1′-biphenyl]-4-carbonitrile (1e)-Based Compounds 4a–n^a.

^aReagents and conditions: (A) for compounds 1e–g where X is −Br, substituted 4-hydroxybenzaldehde, K₂CO₃, DMF, rt, overnight (88% for 4a, 61% for 4g, 57% for 4i, and 52% for 4m); for compounds 1b, 1d where X is −OH, (1) SOCl₂, DCM, 40 °C, (2) substituted 4-hydroxybenzaldehde, K₂CO₃, DMF, rt, overnight (30% for 4c and 60% for 4e); (B) for compounds 4a,c,e,g,i, amine component, NaBH₃CN, AcOH, DMF, rt, overnight (43% for 4b, 61% for 4d, 37% for 4f, 26% for 4h, 44% for 4j, 67% for 4k, and 33% for 4l); for compounds 4m, (1) SOCl₂, DCM, 40 °C, (2) amine component, K₂CO₃, DMF, rt, overnight (29% for 4n).