ChemicalBook CAS DataBase List 5-BroMo-1-Methyl-1H-benzo[d][1,2,3]triazole

5-BroMo-1-Methyl-1H-benzo[d][1,2,3]triazole synthesis

5synthesis methods

Product Name:5-BroMo-1-Methyl-1H-benzo[d][1,2,3]triazole
CAS Number:944718-31-4
Molecular formula:C7H6BrN3
Molecular Weight:212.05

69038-76-2

944718-31-4

General procedure for the synthesis of 5-bromo-1-methyl-1H-benzo[d][1,2,3]triazole from 4-bromo-N1-methylbenzene-1,2-diamine: 5-bromo-1-methyl-7H-benzo[2 (1.52 g, 22 mmol) was dissolved in water (5 ml) at 0 °C. The resulting solution was stirred at 0-10°C for 4 h. The pH was adjusted to 8 with potassium hydroxide (3N) and extracted with dichloromethane (2 x 200 ml). The organic layers were combined and concentrated in vacuum to give the residue. The residue was purified by silica gel chromatography (eluent: petroleum ether solution of 50% dichloromethane) to afford 5-bromo-1-methyl-1H-benzo[d][1,2,3]triazole as a red solid (1.5 g, 31% yield).LC/MS (ESI, m/z): [M + H]+ 213.1.1.1H-NMR (300 MHz, CDCl3) δ 8.24-8.25 (m, 1H), 7.60-7.63 (m, 1H), 7.42-7.46 (m, 1H), 4.32 (d, J = 5.4 Hz, 3H).

69038-76-2 Synthesis

69038-76-2
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$28.00/100mg

944718-31-4
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$45.00/10mg

Yield:944718-31-4 31%

Reaction Conditions:

Stage #1: 2-N-methylamino-5-bromoanilinewith hydrogenchloride;sodium nitrite in water at 0 - 10; for 4 h;
Stage #2: with potassium hydroxide in water; pH=8;

Steps:

95.3

Ste 3. 5-Bromo-l-methyl-7H-benzo[2 (1.52 g, 22 mmol) in water (5 ml) at 0°C. The resulting solution was stirred for 4 h at 0-10°C, adjusted to pH 8 with potassium hydroxide (3N), extracted with dichloromethane (2 x 200 ml), and the organic layers combined and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (50% dichloromethane in petroleum ether) to afford 5-bromo-l-methyl-iH- benzo[if|[l,2,3]triazole as a red solid (1.5 g , 31 %).LC/MS (ES, m/z): [M+H]⁺.213.1 'H-NMR (300 MHz, CDCI₃) δ 8.24 - 8.25 (m, 1H), 7.60 - 7.63 (m, 1H), 7.42 - 7.46 (m, 1H), 4.32 (d, 7 = 5.4 Hz, 3H)

References:

WO2012/119046,2012,A2 Location in patent:Page/Page column 207-208