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31236-94-9

2-bromocyclododecanone synthesis

11synthesis methods
-

Yield:31236-94-9 126 mg

Reaction Conditions:

with oxone;2-iodo-3,4,5,6-tetramethylbenzoic acid in water;acetonitrile at 25 - 30; for 24 h;

Steps:

4.1 General procedures for α-bromoketones and α-azidoketones from olefins

General procedure: To a solution of the olefin (0.5-1.2mmol) in 10-16mL of acetonitrile-water (1:1) mixture was added NBS (1.05equiv) at rt. The reaction mixture was stirred until all the olefin was consumed, as monitored by TLC analysis. Subsequently, TetMe-IA (10mol%) and Oxone (1.0equiv) were introduced into the reaction mixture, and the stirring was continued. After completion of the oxidation as judged by TLC analysis, the reaction mixture was washed with saturated NaHCO3 solution. The organic matter was extracted 2-3 times with ethyl acetate or dichloromethane, and the combined organic extract was dried over anhyd Na2SO4. The solvent was removed in vacuo and the resultant residue was subjected to a short-pad silica gel column chromatography to isolate pure α-bromoketone.

References:

Chandra, Ajeet;Parida, Keshaba Nanda;Moorthy, Jarugu Narasimha [Tetrahedron,2017,vol. 73,# 40,p. 5827 - 5832]

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