Imidazole → 1-(4-Iodobutyl)-4-methoxybenzene

Temperature

65 °C

To a stirred solution of 4-(4-methoxyphenyl)butan-1-ol (9.37 g, 52 mmol, Aldrich) in dry toluene (185 mL) under an argon atmosphere was added triphenylphosphine (17.8 g, 67.6 mmol) and imidazole (10.6 g, 156 mmol). After ten minutes I2 (17.1 g, 67.6 mmol) was added. The reaction was then heated at 65 ° C. for 30 minutes. Upon cooling to room temperature the reaction was concentrated to 1/4 volume. The remaining solution was diluted with Et2O and washed with H2O and brine and dried (MgSO4). The solvent was removed and the resulting residue was dissolved in CH2Cl2 and applied to a flash chromatography column (silica). Elution with 2% EtOAc in hexane provided a colorless oil: 1H NMR (250 MHz, CDCl3) δ7.08 (d, J=8.7 Hz, 2H, phenyl), 6.82 (d, J=8.7 Hz, 2H, phenyl), 3.78 (s, 3H, OMe), 3.17 (t, J=7.4 Hz, 2H, I-CH2), 2.54 (t, J=7.2 Hz, 2H, benzylic), 1.85 (m, 2H, CH2), 160 (m, 2H, CH2).

1. temperatureUpon cooling to room temperature the reaction
2. concentrationwas concentrated to 1/4 volume
3. additionThe remaining solution was diluted with Et2O
4. washwashed with H2O and brine
5. dry with materialdried (MgSO4)
6. customThe solvent was removed
7. dissolutionthe resulting residue was dissolved in CH2Cl2
8. washElution with 2% EtOAc in hexane
9. customprovided a colorless oil

ORD record

ord-d9c28a2e46f74787a3d615590b3bb843

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05643914