ChemicalBook CAS DataBase List 5-Bromo-1H-benzimidazole

5-Bromo-1H-benzimidazole synthesis

14synthesis methods

Product Name:5-Bromo-1H-benzimidazole
CAS Number:4887-88-1
Molecular formula:C7H5BrN2
Molecular Weight:197.03

1575-37-7
366 suppliers
$10.00/1g

149-73-5 Synthesis

149-73-5
523 suppliers
$12.00/5g

4887-88-1
188 suppliers
$5.00/100mg

Yield:4887-88-1 100%

Reaction Conditions:

Stage #1:4-Bromo-benzene-1,2-diamine;trimethyl orthoformate with hydrogenchloride in water;N,N-dimethyl-formamide at 20; for 1 h;
Stage #2: with sodium hydrogencarbonate in water;N,N-dimethyl-formamide; pH=7

Steps:

87.87a
Step 87a: 7¾rt-butyl 5-bromo-lH-benzo[d]imidazole-l-carboxylate (Compound 0601-187)To a solution of 4-bromobenzene-l,2-diamine (3 g, 16 mmol) in DMF (22 mL) were added trimethyl orthoformate (44 mL) and cone. HC1 (1.5 mL) and the mixture was stirred at room temperature for 1 h. The mixture was diluted with water (200 mL) and adjusted to pH7 with saturated aqueous NaHC0₃, extract with ethyl acetate (200 mL). The organic layer was dried over Na₂S0₄, concentrated to give 5-bromo-lH-benzo[d]imidazole (3.25 g, 100%) as an off-white solid. LCMS: 197 [M+l]⁺. 1H NMR (400 MHz, DMSO-<¾) δ 7.33 (t, J= 8.8 Hz, 1H), 7.55 (dd, J_; = 7.6 Hz, J= 40 Hz, 1H), 7.79 (d, J= 47.2 Hz, 1H), 8.26 (s, 1H), 12.61 (d, J= 25.6 Hz, 1H).

References:

CURIS, INC.;BAO, Rudi;LAI, Chengjung;QIAN, Changgeng WO2011/130628, 2011, A1 Location in patent:Page/Page column 228

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122-51-0 Synthesis