New synthesis of 3-bromoflavones via bromination of 1-(2-hydroxyphenyl)-3- arylpropane-1,3-dione by CuBr2, and conversion into 3-aminoflavones

Chemistry Letters

Volumn 36, Issue 4, 2007, Pages 522-523

  Miyake, Hideyoshi ^a   Nishino, Shouko ^a   Nishimura, Akinori ^a   Sasaki, Mitsura ^a  

^a KOBE UNIVERSITY   (Japan)

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EID: 34248536294     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.522     Document Type: Article

References (23)

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22. 4, and the solvent was removed under reduced pressure. The residue was recrystallized from methanol to give 4b (3.7 g, 15 mmol) in 54% yield. Synthesis of 6b. A DMF (6mL) solution of 4b (0.76 g, 3.0 mmol) was heated to 130°C. Copper(II) bromide (2.68 g, 12 mmol) was added to the solution and stirred for 10 min. The mixture was poured into water and extracted with ethyl acetate. After the usual workup, the crude product was purified by column chromatography on silica gel to give 6b (0.66 g, 2.1 mmol) in 70% yield.
23. 3 to give 8c (0.098 g, 0.26 mmol) in 88% yield. In the cases of 8a and 8e (Entries 1, 5, and 6), a large excess (10-20 equiv.) of amines was used.