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Chemical Structure| 171256-81-8 Chemical Structure| 171256-81-8

Structure of 171256-81-8

Chemical Structure| 171256-81-8

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Product Details of [ 171256-81-8 ]

CAS No. :171256-81-8
Formula : C7H3Cl2IO
M.W : 300.91
SMILES Code : O=C(Cl)C1=CC(Cl)=CC=C1I

Safety of [ 171256-81-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 171256-81-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 171256-81-8 ]

[ 171256-81-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 13421-00-6 ]
  • [ 171256-81-8 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; In toluene; at 100℃; for 3h; General procedure: To a solution of <strong>[13421-00-6]5-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong></strong> (3.0 g, 10.6 mmol) in toluene (150 mL), SOd2(7.75 mL, 106 mmol) was added and the mixture was heated at 100C for 3 hours. Thesolvent was concentrated in vacuum and the residue was co-evaporated from toluene twiceto give the title compound as a grey solid. Yield (3.2 g, 100%). 1H NMR (400 MHz, CDCl3): 6 7.26 (dd, 1 H), 7.98 (d, 1 H), 8.03 (d, 1 H).
100% With thionyl chloride; In toluene; at 100℃; for 3h; To a solution of <strong>[13421-00-6]5-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong></strong> (3.0 g, 10.6 mmol) in toluene (150 mL), SOCl2 (7.75 mL, 106 mmol) was added and the mixture was heated at 100 C. for 3 hours. The solvent was concentrated in vacuum and the residue was co-evaporated from toluene twice to give the title compound as a grey solid. Yield (3.2 g, 100%) [0177] 1H NMR (400 MHz, CDCl3): delta 7.26 (dd, 1H), 7.98 (d, 1H), 8.03 (d, 1H).
With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; for 12h;Heating / reflux; 5-Chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong> (2.8 g, 10 mmol) was taken up in dry methylene chloride (80 mL) and DMF (50 muL, cat.) followed by thionyl chloride (2.4 g, 20 mmol) were added. The mixture was stirred at reflux for 12 h, cooled to room temperature and evaporated in vacuo. The residue was azeotroped with toluene (2×10 mL) and used without further purification. The 5-chloro-2-iodobenzoyl chloride (10 mmol) was taken up in dry methylene chloride (50 mL) and N,O-dimethylhydroxylamine hydrochloride (1.1 g, 11 mmol) was added. The mixture was cooled to 0 C., and pyridine (2.4 g, 30 mmol) was added. The mixture was allowed to warm to room temperature, stir for 12 h, and was then quenched with saturated brine (20 mL). The organic phase was separated and the water phase was extracted with methylene chloride (2×10 mL). The combined organic extracts were dried with anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified using flash chromatography on silica gel (50 g) using methylene chloride as eluent to provide 5-chloro-2-iodo-N-methoxy-N-methylbenzamide (3.1 g, 95%) MS m/z=326 (M+H).
With thionyl chloride; N,N-dimethyl-formamide; at 23℃; for 0.5h; A solution of S-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong> (3.0 g,10.62 mmol), 50C12 (12 mE) and DMF (0.6 mE) was gently warmed with a heat gun until the mixture became homogeneous (15 mm). The solution was maintained at 23 C. for additional 30 mm and then the solution was concentrated. MeOH (24 mE) was added to the crude residue and the solution was maintained at 23 C. for 30 mm. The solution was concentrated and the residue was purified by flash chromatography on l3iotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85: 15) to afford methyl S-chloro-2-io- dobenzoate (3.02 g, 10.20 mmol, 96%).
With thionyl chloride; for 2h;Reflux; According to the procedure reported by Yu and co-workers [3], palladium acetate (22 mg, 0.10mmol), iodobenzene diacetate (644 mg, 2.0 mmol), iodine (507 mg, 2.0 mmol), and tetrabutylammonium iodine (739 mmol, 2.0 mmol) were added to a solution of 3-chloro<strong>[13421-00-6]benzoic acid</strong> (313 mg, 2.0 mmol) in 1,2-dichloroethane (20 mL). The mixture was heated at 100 C with stirring for 2 h and then allowed to cool to room temperature. Iodobenzene diacetate (644 mg, 2.0 mmol) and iodine (507 mg, 2.0 mmol) were added to the mixture. After stirring at 100 C for 4 h, the resulting mixture was diluted with10% sodium carbonate. The aqueous layer was separated, washed with Et2O, and then acidified with 10% HCl. The resulting mixture was extracted with EtOAc and the organic layer was dried over Na2SO4; filtered; and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/EtOAc = 4/1) to give crude <strong>[13421-00-6]5-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong></strong> (223 mg) as a colorless solid, which was suspended in thionyl chloride (2 mL). After stirring under reflux conditions for 2 h, the resulting mixture was concentrated under reduced pressure. The remaining thionyl chloride was removed by azeotropic distillation with benzene. The residue was dissolved in anhydrous CH2Cl2 (3 mL). To the mixture were added isopropylamine (56 mg, 0.95 mmol) and triethylamine (240 mg,2.37 mmol) at 0 C under a nitrogen atmosphere. After stirring at room temperature for 13 h, the resulting solution was diluted with EtOAc. The mixture was washed with 10% HCl, saturated aqueous NaHCO3, water, and brine; dried overNa2SO4; filtered; and concentrated under reduced pressure. The residue was purified by recrystallization from hexaneand CHCl3 to give 19 (138 mg, 21% in 3 steps) as colorless needles.

 

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