A new useful entry of IBX: The synthesis and structure of α-(2-iodobenzoyloxy)ketones

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4101-4104

  Pan, Zhen Liang ^a   Liu, Xue Yuan ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Functionalized ketones; Hypervalent iodine IBX; Structure; Synthesis

Indexed keywords

BENZOIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 2342559306     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.158     Document Type: Article

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46. The typical procedure is as follows: Potassium iodide (2 mmol) and ketones (1 mmol for entries of bi-substituted products, 2 mmol for entries of mono-substituted products) were sequentially added to a suspension of IBX (2 mmol) in acetonitrile (15 mL). The red color appeared soon and the resulting mixture was heated to reflux under stirring for 15-20 h. The reaction was monitored by TLC (thin layer chromatography) until it complete. The mixture was allowed to cool and then quenched with sodium thiosulfate (5% aqueous solution, 20 mL). The mixture was transferred to a separating funnel and extracted with dichloromethane (3 × 20 mL). The organic phase was combined and sequentially washed with NaOH (5% aqueous solution, 2 × 30 mL), brine (2 × 30 mL) and dried over anhydrous sodium sulfate. The solvent was removed at reduced pressure. The resulting product was purified by column chromatography (hexane/ethyl acetate 30/1) to give oil liquid or solid