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-8ad3e346f50746bc81bc84d5ea1bcb29

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610723B2