Methyl o-iodobenzoate

Ethyl o-iodobenzoate Methyl o-iodobenzoate Ethyl m-iodobenzoate Methyl m-iodobenzoate Ethyl p-iodobenzoate Methyl p-iodobenzoate... 

Methyl o-iodobenzoate is converted under these conditions (equation 11) into methyl salicylate (main product) and dimethyl diphenate (minor product). If the cuprous salt is replaced by the cupric salt, hydrolysis is essentially the only reaction (equation III). If ammonium tetrafluoroborate is added, methyl benzoate is the only product. 

Methyl o-iodobenzoate, 130, 132 Methyl isobutyl ketone, 652 Methyl itaconate, 366... 

Reaction of o-iodoaniline (33) with internal alkynes offers a good synthetic method of substituted indoles [13], A practical synthesis of psilocin was carried out by utilizing the reaction of the iodoaniline derivative 34 with internal alkyne to form an indole derivative as a key reaction [14], The thieno[3.2- ]pyrrole 37 was obtained by the reaction of 2-iodo-3-aminothiophene (35) with the alkyne 36 [15], These reactions of aryl iodides proceed in the absence of phosphine ligands. The isocoumarin 39 was obtained by the reaction of methyl o-iodobenzoate (38). Poor yield was obtained when the free acid was used [11]. 

Lactone products can also be formed via Grignard-type addition to aldehydes from o-iodobenzoates [116]. The Cheng group developed an enantioselective Co-catalyzed method for preparation of 5-membered phthalide products from methyl o-iodobenzoate and aldehydes (Scheme 2.61). While Ni and Pd catalysts were ineffective, the authors propose a Co(I)/Co(III) mechanism involving oxidative addition of the sp C—I bond followed by addition and ring closure [116]. Co(III) is reduced to Co(I) by the zinc metal present in solution. 

The submitters used a two-necked, round-bottomed flask equipped with a magnetic stirbar, three-way stopcock connected to vacuum and a N2 source, and a solid addition tube. The addition tube was charged with methyl 4-iodobenzoate, tris(dibenzylideneacetone)dipalladium(0), and tri-o-tolylphosphine. After the zinc reagent was formed and the ice bath was removed, the solids contained in the addition tube were added in one portion by inverting the tube. 

Methyl 4-iodobenzoate was purchased from Avocado Chemical Co. Zinc dust (< 10 microns, 95% purity) was purchased from Aldrich Chemical Company, Inc. The checkers purchased Pd2dba3 and P(o-Tol)3 from Strem Chemicals, Inc. and I2 from Mallinckrodt. The submitters purchased Pd2dba3 and P(o-Tol)3 from Aldrich Chemical Company, Inc. 

In 2011, Bhanage and co-workers reported a carbon monoxide-free one-step synthesis of phthalimides by using formamides as an amine and CO source. With POCI3 as the activator, various phthalimides were produced in moderate to excellent yields (Scheme 2.2). In addition to 1,2-dihalobenzenes, 2-iodobenzoic acid and methyl 2-iodobenzoate can be applied as substrates for phthalimide preparation with formamides as an amine and CO source as well. This methodology was extended and applied in the synthesis of isobenzofuran-l(3/f)-one (70% yield) by using o-iodoben l alcohol as the substrate. 

Several solid supports have been employed for the attachment of o-iodosobenzoic acid, including silica gel, titania and nylon [89]. Two polymer-supported o-iodoxybenzoic acid reagents have recently been reported. The first was obtained by attaching a carboxymethyloxy derivative of f-butyl o-iodo-benzoate to an aminopropylated silica gel and oxidation with oxone [90]. The second involved chloromethylated polystyrene which was coupled with methyl 5-hydroxy-2-iodobenzoate and eventually oxidized by Bu4NS05H/MeS03H [91]. Some of these polymeric reagents appear in Scheme 31. 

---