Boron tribromide → HCID 71547820, compound

Temperature

0 °C

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]+.

1. customquenched with saturated NaHCO3 solution (10 mL)
2. extractionextracted with DCM (2×100 mL)
3. washThe combined organic extracts were washed with brine solution (10 mL)
4. dry with materialthe organic layer was dried over Na2SO4
5. concentrationconcentrated under vacuum
6. customto obtain crude product
7. washThe crude product was washed with pentane (10 mL)

ORD record

ord-5fd3c08f8fe1459d913aeb3b909ebce5

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2