ChemicalBook CAS DataBase List 6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE

6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE synthesis

6synthesis methods

Product Name:6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE
CAS Number:53484-16-5
Molecular formula:C8H7BrN2
Molecular Weight:211.06

64-18-6 Synthesis

64-18-6
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302800-13-1
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$13.00/250mg

53484-16-5
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$35.00/250mg

Yield: 98%

Reaction Conditions:

with iron;ammonium chloride in isopropyl alcohol for 24 h;Reflux;

Steps:

45.B Step B: Preparation of 6-bromo-1-methyl-benzimidazole
[0444j Step B: Preparation of 6-bromo-1-methyl-benzimidazole: A mixture of 5- bromo-N-methyl-2-nitro-aniline (6.0 g, 26 mmol), iron powder (14.5 g, 260 mmol), ammonium chloride (13.9 g, 260 mmol) and formic acid (49.0 mL, 1298 mmol) in 2- propanol (75 mL) was stirred under reflux for 24 hours. After cooling to ambient temperature, ethyl acetate (50 mL) was added. The solid was removed by filtering through a pad of celite. The filtrate was concentrated. Saturated sodium bicarbonate (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography on silica gel 10:1 ethyl acetate/MeOH to give 6-bromo-1-methyl-benzimidazole (5.35 g, 98%) as solid.

References:

PELOTON THERAPEUTICS, INC.;DIXON, Darryl, David;GRINA, Jonas;JOSEY, John, A.;RIZZI, James, P.;SCHLACHTER, Stephen, T.;WALLACE, Eli, M.;WANG, Bin;WEHN, Paul;YANG, Hanbiao WO2015/175845, 2015, A1 Location in patent:Paragraph 0444