Efficient and convenient oxidation of organic halides to carbonyl compounds by H2O2 in ethanol

Tetrahedron Letters

Volumn 48, Issue 11, 2007, Pages 1919-1921

  Tang, Jingting ^a   Zhu, Jinlong ^a   Shen, Zongxuan ^a   Zhang, Yawen ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Aldehyde; Hydrogen peroxide; Ketone; Organic halide; Oxidation

Indexed keywords

ALCOHOL; ALDEHYDE; BROMIDE; CARBONYL DERIVATIVE; CHLORIDE; HYDROGEN PEROXIDE; KETONE DERIVATIVE; ORGANOHALOGEN DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; OXIDATION KINETICS; REACTION ANALYSIS;

EID: 33846936791     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.084     Document Type: Article

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20. General procedure for the oxidation of organic bromides to carbonyl compounds using benzyl bromide as an example: Benzyl bromide (340 g, 2.0 mmol) was taken in a round bottom flask along with hydrogen peroxide (30%, 2 mL). The above mixture was dissolved in 15 mL of ethanol and the mixture was heated at reflux. The progress of the reaction was monitored by thin layer chromatography. The reaction was completed in 3 h. The ethanol was removed under reduced pressure and the residue was treated with 20 mL of water and then extracted with ethyl acetate (2 × 30 mL). The combined ester layers were dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed to give the desired product.
21. General procedure for the oxidation of organic chlorides to carbonyl compounds: To a round bottom flask was added benzyl chloride (250 mg, 2.0 mmol), KBr (24 mg, 0.2 mmol), and hydrogen peroxide (30%, 2 mL) in 15 mL ethanol. The mixture was refluxed for the time given in Table 2 and worked up as described for the oxidation of organic bromides.
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