Boron tribromide → HCID 71547820, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(1-(5-(4-methoxyphenyl)thiophen-2-yl)propyl)-1H-imidazole (45 mg, 0.15 mmol; prepared as described in Example 3) in DCM (4 mL) was added BBr3 (0.02 mL, 0.22 mmol) at 0° C. The reaction was stirred at 0° C. for about 2 h, quenched with saturated NaHCO3 solution (10 mL), and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was washed with pentane (10 mL) afforded 4-(5-(1-(1H-imidazol-1-yl)propyl)thiophen-2-yl)phenol as off white solid (42 mg, 81.3% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.59 (s, 1H), 7.78 (s, 1H), 7.37 (d, 2H), 7.25 (s, 1H), 7.14 (d, 1H), 7.01 (d, 1H), 6.90 (s, 1H), 6.75 (d, 2H), 5.47 (t, 1H), 2.31-2.16 (m, 2H), 0.80 (t, 3H), LC-MS m/z calcd for [M−H]+ 285.10. found 217.2 [M-imidazole]+.

Provenance & Evidence