Benzimidazole → 1-(3-Bromo-1-propyl)benzimidazole

To a solution of benzimidazol (355 mg, 3.00 mmol) in dry DMF (10 mL) was added NaH (83 mg, 3.3 mmol) at 20° C. under N2 atmosphere. The reaction mixture was stirred for 30 min, and then 1,3-dibromopropane (1.82 g, 9.00 mmol) was added and stirres for additional 15 h at 20° C. The reaction was quenched by addition H2O, and the product was extracted with EtOAc. The organic solution was then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. 1-(3-Bromo-1-propyl)benzimidazole (530 mg, 74%) was isolated by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a pale yellow oil. 1H NMR (CDCl3, 300 MHz) δ2.40 (qu, 2H, J=6.6 Hz), 3.33 (t, 2H, J=6.2 Hz), 4.42 (t, 2H, J=6.6 Hz), 7.12-7.20 (m, 1H), 7.27-7.48 (m, 2H), 7.43-7.49 (m, 1H), 7.78-7.86 (m, 1H) ppm.

1. waitstirres for additional 15 h at 20° C
2. customThe reaction was quenched by addition H2O
3. extractionthe product was extracted with EtOAc
4. washThe organic solution was then washed with H2O and brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-caf3c9c9984143cb95f2549723f92da5

Quelldatensatz

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

USRE039679E1