N-bromobutanimide → (5-bromo-1-methyl-1H-imidazol-2-yl)methanol

1-Methylimidazole-2-methanol (3.15 g; 28 mmol) (R. J. Sundberg; P. V. Nguyen; Med. Chem. Res. 7, 2, 1997, 123-136) was suspensed in THF (75 ml) at −20° C. and treated slowly (within 30 min) with N-bromosuccinimide (4.9 g, 27 mmol). The reaction mixture was allowed to warm up slowly to room temperature and quenched with saturated aqueous NaHCO3 solution (50 ml). The aqueous layer was extracted 3 times with AcOEt. The combined extracts were washed with saturated aqueous NaHCO3 solution, dried, over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed (silica, elution first with AcOEt/hexane=1:1, then with CH2Cl2/MeOH=95:05) to provide the title compound (2.11 g, 67%) as a white solid. MS: m/e=191.2 (M+).

1. customquenched with saturated aqueous NaHCO3 solution (50 ml)
2. extractionThe aqueous layer was extracted 3 times with AcOEt
3. washThe combined extracts were washed with saturated aqueous NaHCO3 solution
4. dry with materialdried, over Na2SO4
5. filtrationfiltered
6. customthe solvent was removed in vacuo
7. customThe residue was chromatographed (
8. washsilica, elution first with AcOEt/hexane=1:1

ORD record

ord-4d417752ae244f4f93c0d0ff86060e71

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06667335B2