2-Bromo-1-methyl-1H-imidazole

Uses

2-Bromo-1-methylimidazole is used in in pharmaceuticals, drug candidates, ligands for transition metal catalysts and other molecular functional materials.

Uses

2-Bromo-1-methyl-1H-imidazole can be used in the synthesis of the following:

• N-(4-methoxyphenyl)-1-methyl-1H-imidazol-2-amine via C-N coupling with p-anisidine
• 1,2-bis[2-methyl-5-(1-methyl-1H-imidazol-2-yl)-3-thienyl]-cyclopentene, a ligand which can form bimetallic platinum(II) complex with potent cytotoxic activity

Synthesis

616-47-7

16681-59-7

General procedure for the synthesis of 2-bromo-1-methyl-1H-imidazole from N-methylimidazole: 1-methylimidazole (1 mmol, 82.1 mg) and carbon tetrabromide (1.1 mmol, 364.8 mg) were added to a 10 mL round bottom flask. Subsequently, 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg) were added and the reaction was stirred at room temperature for 3 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was poured into water and extracted with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate and the dichloromethane was removed by rotary evaporator to give the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate (v/v=10:1) as the eluent, and finally 2-bromo-1-methyl-1H-imidazole (reddish brown liquid, 101.4 mg, 63% yield) was obtained.

References

[1] Chemical Communications, 2013, vol. 49, # 37, p. 3875 - 3877
[2] Australian Journal of Chemistry, 1999, vol. 52, # 3, p. 159 - 165
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[4] Patent: CN107501023, 2017, A. Location in patent: Paragraph 0055; 0056
[5] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665