ChemicalBook CAS DataBase List 1-(3-bromopropyl)-1H-benzo[d][1,2,3]triazole-5-carbaldehyde

1-(3-bromopropyl)-1H-benzo[d][1,2,3]triazole-5-carbaldehyde synthesis

5synthesis methods

Product Name:1-(3-bromopropyl)-1H-benzo[d][1,2,3]triazole-5-carbaldehyde
CAS Number:1435049-23-2
Molecular formula:C10H10BrN3O
Molecular Weight:268.11

1-(3-hydroxypropyl)-1H-benzo[d][1,2,3]triazole-5-carbaldehyde

1435049-22-1
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1-(3-bromopropyl)-1H-benzo[d][1,2,3]triazole-5-carbaldehyde

1435049-23-2
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Yield:1435049-23-2 195 mg

Reaction Conditions:

with carbon tetrabromide;triphenylphosphine in dichloromethane at 20; for 3.5 h;Cooling with ice;

Steps:

Intermediate 20.1 -(3-bromopropyl)-1 H-1 ,2,3-benzotriazole-5-carbaldehyde

200 mg (0.975 mmol) of 1 -(3-bromopropyl)-1 H-1 ,2,3-benzotriazole-5-carbaldehyde (Intermediate 19) are dissolved in 10.5 ml of dichloromethane. 388 mg (1.17 mmol) of carbon tetrabromide are added and the solution cooled externally with an ice/water bath. 307 mg (1.17 mmol) of triphenylphosphine are slowly added and the system is stirred for 20 min with external cooling and 2 hr at rt. After addition of 0.5 more equivalents of both carbon tetrabromide and triphenylphosphine and additional stirring for 10 min with the external cooling and 1 hr at rt the solvents are eliminated in vacuo and the residue is chromatographically purified over silicagel eluting with hexane/ethyl ether (100/0 to 0/100). 195 mg of pure title compound are obtained (74 % yield).

References:

WO2013/68552,2013,A1 Location in patent:Page/Page column 46

1435049-21-0 Synthesis