Imidazole → 1-(3-Bromopropyl)-1H-imidazole

To a stirred solution of imidazole (500 mg, 7.35 mmol) and 1,3-dibromopropane (2.2 mL, 22.0) in THF (35 mL) was added 60% NaH (356 mg, 8.82 mmol), and the resultant mixture was refluxed for 1 h and stirred at room temperature overnight. The mixture was quenched with H2O (25 mL) and diluted with CH2Cl2 (40 mL). The aqueous phase was separated and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to dryness. Purification by flash chromatography on silica gel (CH2Cl2/MeOH, 97:3) provided 1-(3-Bromo-propyl)-1H-imidazole (410 mg, 30%) as a colorless oil. 1H NMR (CDCl3) δ 2.20-2.34 (m, 2H), 3.31 (t, 2H, J=6.3 Hz), 4.16 (t, 2H, J=6.2 Hz), 6.93 (s, 1H), 7.08 (s, 1H), 7.51 (s, 1H).

1. customThe mixture was quenched with H2O (25 mL)
2. additiondiluted with CH2Cl2 (40 mL)
3. customThe aqueous phase was separated
4. extractionextracted with CH2Cl2 (3×15 mL)
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated to dryness
8. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH, 97:3)

ORD record

ord-5e18d3597c814e759d3eb303dda0f79f

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501518B2