62069-34-5

Usage

Preparation

Preparation by addition of an aqueous iodine and potassium iodide solution on resacetophenone in 30% ammonium hydroxide solution at r.t. (93%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Downstream Products

• 62069-33-4 1-(2,4-dihydroxy-5-iodophenyl)ethanone 
• 532-48-9 1-(6-hydroxy-2-isopropenyl-benzofuran-5-yl)-ethanone 
• 103040-69-3 1-(3,5-diiodo-2,4-dimethoxy-phenyl)-ethanone 

Relevant academic research and scientific papers

Synthesis and Transformation of 5-Acetyl-2-aryl-6-hydroxybenzofurans into Furanoflavanone Derivatives

Tandem palladium-catalyzed Sonogashira cross-coupling and heteroannulation of 3-bromo-2,4-dihydroxy-5-iodoacetophenone with arylacetylenes followed by the base-mediated Claisen-Schmidt aldol condensation of the intermediate 5-acetyl-2-aryl-7-bromo-6-hydro

Synthesis of isobavachalcone and some organometallic derivatives

Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.

Synthesis, characterization, X-ray structural analysis, and iodination ability of benzyl(triphenyl)phosphonium dichloroiodate

Benzyl(triphenyl)phosphonium dichloroiodate (BTPPICl2), BnPh3P+(ICl2)-, is easily synthesized in a nearly quantitative yield by the addition of BnPh 3P+Cl- to a CH2Cl2 solution of iodine monochloride (ICl). BnPh3P+Cl - can be prepared by the reaction of Ph3P and BnCl. The compound was characterized by physicochemical and spectroscopic methods (elemental analysis, FT-IR, and 1H-NMR). The use of phosphonium counterion improves the quality of the BTPPICl2 crystals. BTPPICl2 crystallizes in the monoclinic system, and its crystal and molecular structure has been determined at 100(1) K by X-ray diffraction. The structure was solved by the direct method and had refined R value of 0.0637 for 699 reflections (I>2σ(I)), space group P21/n with a=12.4700(3), b=13.2196(3), c=14.4580(3) A, β=102.6340(10)°, V=2325.67(9) A3, and Z=4. The I-atom is coordinated by two Cl-atoms as ligands in a linear geometry. This compound is a versatile reagent for the efficient and selective iodination of organic substrates, in particular of aromatic phenols to the corresponding iodo compounds, under mild conditions. To assess the generality of method, a wide variety of phenols with electron-donating and electron-withdrawing substituents were studied. BTPPICl2 is a mild iodination reagent, which offers a new avenue for an expeditious iodination of phenols. The inexpensive, relatively non-toxic reagent, and mild conditions are the positive features of the procedure and reagent. Copyright

Total synthesis confirms laetirobin as a formal diels-alder adduct

Laetirobin, isolated from a parasitic fungus host-plant relationship, was synthesized in six practical steps with an overall yield of 12% from commercially available 2,4-dihydroxyacetophenone. Because the product is a pseudosymmetric tetramer of benzo[b]-

A simple and efficient method for solvent-free iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid by grinding method

Green, mild and efficient iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid in the solid-state by grinding under solvent-free conditions at room temperature. This method provides several advantages such as environmentally friendly, short reaction times, high yields, non-hazardous and simple work-up procedure.

Pyridinium lodochloride: An efficient reagent for lodination of hydroxylated aromatic ketones and aldehydes

Direct iodination of several reactive aromatic compounds like hydroxy substituted acetophenones and aldehydes with pyridinium iodochloride (PyICl) proceeded smoothly to afford the corresponding aromatic iodides in good to excellent yield. Pyridinium iodochloride has been found to be an efficient solid iodinating reagent with no hazardous effect and it can be handled safely.

SYTHESIS OF ISOEUPARIN, A BENZOFURAN EXTRACTIVE OF TAGETES PATULA

The structure of isoeuparin, a constituent isolated from seedlings of Tagetes patula, is confirmed by a short synthesis, involving reaction of cuprous isopropenylacetylide with 2,4-dihydroxy-3-iodoacetophenone.Key Word Index - Tagetes patula; Compositae;

Syntheses of the Natural Dibenzofuran, Ruscodibenzofuran

Short syntheses of the natural dibenzofuran, ruscodibenzofuran (1) from readily available phenols are described.The key step involve initial formation of a 2-isopropenylbenzofuran by reaction of an ortho-halogenophenol with cuprous isopropenylacetylide fo