ChemicalBook CAS DataBase List 4-BroMo-1-(iso-propyl)-1H-iMidazole

4-BroMo-1-(iso-propyl)-1H-iMidazole synthesis

4synthesis methods

Product Name:4-BroMo-1-(iso-propyl)-1H-iMidazole
CAS Number:623577-60-6
Molecular formula:C6H9BrN2
Molecular Weight:189.05

75-26-3
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$10.00/10g

623577-60-6
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$45.00/10mg

Yield:623577-60-6 30%

Reaction Conditions:

Stage #1: 4-bromo-1 H-imidazolewith sodium hydride in N,N-dimethyl-formamide at 0 - 20; for 0.5 h;
Stage #2: isopropyl bromide in N,N-dimethyl-formamide at 20; for 15 h;

Steps:

84.1

A mixture of 4-bromo-1H-imidazole (1.0 g, 6.80 mmol) in dimethylformamide (5 mL) was stirred at 0°C, to which was added sodium hydride, 60% suspension in oil, (326 mg, 8.20 mmol). The reaction mixture was warmed to room temperature and stirred for 30 minutes, followed by dropwise addition of 2-bromopropane (0.70 mL, 7.48 mmol). The reaction mixture was stirred at room temperature for 15 hours under nitrogen, then quenched with water (10 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic extracts were washed with water (20 mL) and extracted with 1M hydrochloric acid (3 x 20 mL). The combined acidic extracts were washed with ethyl acetate (20 mL), then basified with ammonium hydroxide (pH 12), and extracted with ethyl acetate (3 x 20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. Preparative HPLC, eluting with an ethyl acetate- isohexane gradient, gave the product as a pale brown oil (380 mg, 30%) 8 (1H, 400MHz, CDCl3) 1.47 (6H, d, J = 6.8Hz), 4.28-4. 32 (1H, m), 6.92 (1H, d, J = 1.5 Hz), 7.40 (1H, d, J = 1.5 Hz). MS (ES+) 189,191 ([MH]+).

References:

WO2003/93252,2003,A1 Location in patent:Page/Page column 117