Boron tribromide → 4-{2-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-ethyl}-benzene-1,2-diol

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Reaction Steps

A procedure similar to that in Example 7 was used. 5-benzyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-(4-methoxy-phenyl)-thiazole prepped in step 4 of Example 77 and boron tribromide were as starting materials, the crude product was recrystallized with acetone to obtain a product as a white solid in a yield of 52.2%, mp: 177-178 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.82 (2H, t, J=8.16 Hz, ArH), 3.11 (2H, t, J=8.16 Hz, ArH), 4.20 (2H, s, CH2), 6.48 (1H, d, J=8.12 Hz, ArH), 6.58˜6.64 (2H, m, ArH), 6.82 (2H, d, J=8.40 Hz, ArH), 7.14˜7.26 (3H, m, ArH), 7.32 (2H, t, J=7.28 Hz, ArH), 7.44 (2H, d, J=8.40 Hz, ArH), 8.69 (1H, s, OH), 8.75 (1H, s, OH), 9.61 (1H, s, OH); EI-MS m/e (%): 403.2 (M+, 67), 281.2 (100); HREI-MS Calcd. for C24H21NO3S: 403.1242. found: 403.1238.

Provenance & Evidence