Imidazole → 3-(3-Methoxyphenyl)propyl iodide

A magnetically stirred solution of 3-(3-methoxyphenyl)propan-1-ol (62.48 g, 375.9 mmol), triphenylphosphine (128.6 g, 490.4 mmol), and imidazole (35.53 g, 516.7 mmol) in anhydrous acetonitrile (300 mL) / anhydrous diethyl ether (600 mL) at 5° C. was treated portion wise with iodine (136.20 g, 536.6 mmol). The yellow suspension turned orange with the last addition. The suspension was stirred 45 min, filtered, the cake washed with fresh diethyl ether (300 mL), the combined filtrate was concentrated in vacuo to 300 mL and diluted with diethyl ether (200 mL). The resultant organic solution was washed with saturated sodium thiosulfate (2×500 mL), saturated cupric sulfate (2×500 mL), brine (2×500 mL), filtered and concentrated in vacuo. The residue was digested with hexanes (300 mL), filtered and concentrated in vacuo. Kugelrohr distillation (0.1 torr, 120° C.) provided the desired product as a yellow liquid (88.10 g, 85%): 1H NMR (CDCl3) δ 7.20 (t, J=8 Hz, 1H), 6.81-6.73 (m, 3H), 3.81 (s, 3H), 3.17 (t, J=8 Hz, 2H), 2.70 (t, J=8 Hz, 2H), 2.14 (quint, J=8 Hz, 2 H).

1. additionThe yellow suspension turned orange with the last addition
2. filtrationfiltered
3. washthe cake washed with fresh diethyl ether (300 mL)
4. concentrationthe combined filtrate was concentrated in vacuo to 300 mL
5. additiondiluted with diethyl ether (200 mL)
6. washThe resultant organic solution was washed with saturated sodium thiosulfate (2×500 mL), saturated cupric sulfate (2×500 mL), brine (2×500 mL)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. distillationKugelrohr distillation (0.1 torr, 120° C.)

ORD record

ord-f486330200e94dd78447cc1aef40ec81

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05541228