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ChemicalBook CAS DataBase List 5-Bromobenzo[c][1,2,5]oxadiazole
51376-06-8

5-Bromobenzo[c][1,2,5]oxadiazole synthesis

6synthesis methods
Triphenylphosphine (1.1 mmol) was dissolved in dry toluene (3 mL) and stirred at 110°C under argon atmosphere; then 6-bromobenzo[c][1,2,5]oxadiazole 1-oxide (1 mmol) in toluene (0.5 mL) was added dropwise over 1 hour and the resulting mixture was stirred for 3 hours. After completion, the solvent was evaporated in vacuo, and the crude was purified through flash column chromatography (cyclohexane - diethyl ether 98:2) to afford 5-Bromobenzo[c][1,2,5]oxadiazole which is a pale pink solid.
5-BROMO-2,1,3-BENZOXADIAZOLE
36387-84-5 Synthesis
5-broMobenzo[c][1,2,5]oxadiazole oxide

36387-84-5
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Yield:51376-06-8 71%

Reaction Conditions:

with triethyl phosphite in ethanol at 60; for 1 h;Inert atmosphere;

Steps:



To a stirred solution of 5-bromobenzo[c][l,2,5]oxadiazole 1-oxide (6.0 g, 28.436 mmol) in ethanol (60 mL) was added triethyl phosphite (6.2 mL, 34.123 mmol) at RT under an inert atmosphere. The reaction mixture was then heated at 60 0C for 1 h., cooled to RT, diluted with hexane (100 mL) and stirred for 10 min. The precipitated solid was filtered off and the filtrate was concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 5- , bromobenzo[c][l,2,5] oxadiazole (4.0 g, 71%) as a light yellow solid.

References:

WO2009/158393,2009,A1 Location in patent:Page/Page column 100

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