5-Iodosalicylaldehyde

General procedure: To a stirred solution of the substrate (1 mmol) in CHIC1 was dissolved in glacial acetic acid to prepare 1 M IC1 glacial acetic acid solution. 96 ml of the prepared IC1 glacial acetic acid solution was placed in a round bottom flask and 9. 76 g (0.08 mil) of salicylaldehyde was added at 40 ° C After the completion of the reaction, the solvent was distilled off under reduced pressure, and the remaining liquid was poured into an aqueous solution of sodium thiosulfate to precipitate a pale yellow solid which was filtered and dried to give Intermediate 117 · 8g (0.072 mol) percentGeneral procedure: The general method for ultrasonically assisted brominationreaction is almost similar to conventional reaction as mentionedabove. A centimolar (0.01 mol) organic substrate (phenols, anilines, or acetanilides), 0.001 mol potassium halide(KBr), about 50 mg of dilute KHSO4, and hypervalent Cr(VI) reagent (IQCC or IQDC) were suspended in about30 mL solvent (DCE or ACN) in a previously cleaned roundbottom(R.B) flask placed in a sonicator. The reaction mixtureis sonicated at room temperature about 30–40 min. Progressof the reaction was monitored by TLC technique. Workupprocedure after completion of the reaction mixture is similarto the one described previously.General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.The synthesis was performed in analogy to Ref. [37]. In aone-neck round-bottom flask a solution of 16.1 g ICl(99.1 mmol) in 100 cm3 DCM (*1 M) was cooled to0 C. Salicylaldehyde (6, 10.0 cm3, 99.1 mmol) dissolvedin 40 cm3 DCM (*2.5 M) was added. The reaction waswarmed to RT and stirred until full conversion wasobserved (24 h). The reaction mixture was diluted with100 cm3 DCM and washed with 1 M Na2S2O3 solution(2 9 100 cm3). The aqueous phase was extracted withDCM (3 9 50 cm3) and the organic layer was then washedwith saturated NaCl solution (1 9 200 cm3). After dryingover Na2SO4 and filtering, the solvent was removed invacuo. Recrystallization from cyclohexane afforded 16.7 g(68 percent) 7 as pale yellow powder. M.p. 97-99 C (Ref. [32];97-99 C); NMR data were found to agree with thosedescribed in Ref. [32].A solution of 250 g (1.54 mol) of iodine chloride in 600 ml of anhydrous dichloromethane is added dropwise over the course of 2 h to a solution of 188 g (1.54 mol) of salicylaldehyde in 1 l of anhydrous dichloromethane in a heat-dried flask under argon. After stirring at RT for 3 days, a saturated aqueous sodium sulfite solution is added with vigorous stirring. The organic phase is separated off, washed once with water and saturated aqueous sodium chloride solution and dried over sodium sulfate. The solvent is evaporated and the residue is recrystallized from ethyl acetate. 216 g (57percent of theory) of the product are obtained. LC-MS (ESI, Method 10): m/z=246 (M-H)Thus, the first step consists of producing 5-iodosalicylaldehyde from salicylaldehyde. (0100) In a 500 mL two-neck flask provided with a condenser, are placed with stirring, 160 mL of glacial acetic acid and 10.4 mL (100 mmol) of salicylaldehyde. A solution of 10 g (1.1 equiv., 110 mmol) of iodine monochloride dissolved in a minimum of acetic acid is then added to the mixture. The reaction is maintained with stirring at T=40° C. for 72 hours. The solvent is then evaporated. The residue is taken up in 100 mL of dichloromethane, washed with 100 mL of an aqueous solution saturated with sodium thiosulfate, 100 mL of a solution saturated with sodium chloride NaCl and 150 mL of distilled water. The organic phase is dried on MgSO[0713] To the mixture of 20 g (91 mmol) of 4-iodophenol and 25.1 g (264 mmol) anhydrous magnesium dichloride in 455 mL of anhydrous acetonitrile was added triethylamine and PARAFORMALDEHYDE. The mixture was heated to reflux for 4 h, allowed to cool to rt and treated with 500 mL of 5percent HCI. The solution was extracted three times with EtOAc. The combined organic extracts were washed with brine (3 x) and dried over anhydrous magnesium sulfate. The dried organic solution was evaporated to afford an oil, which was purified by silica gel chromatography with EtOAc/hexane (2: 8). Concentration of the desired fractions afforded 15 g (66percent) of a yellow solid, which was used directly in the next step without further purification.

Molecular Weight:248.02
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:247.93343
Monoisotopic Mass:247.93343
Topological Polar Surface Area:37.3
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes