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Chemical Structure| 143321-89-5 Chemical Structure| 143321-89-5

Structure of 143321-89-5

Chemical Structure| 143321-89-5

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Product Details of [ 143321-89-5 ]

CAS No. :143321-89-5
Formula : C8H5F3INO
M.W : 315.03
SMILES Code : O=C(NC1=CC=CC=C1I)C(F)(F)F
MDL No. :MFCD00547381

Safety of [ 143321-89-5 ]

Application In Synthesis of [ 143321-89-5 ]

* 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 [ 143321-89-5 ]

[ 143321-89-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 108-86-1 ]
  • [ 143321-89-5 ]
  • [ 536-74-3 ]
  • [ 3469-20-3 ]
  • 2
  • [ 38222-83-2 ]
  • [ 615-43-0 ]
  • [ 143321-89-5 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic anhydride; In dichloromethane; water; Example 6B 2,2,2-Trifluoro-N-(2-iodophenyl)acetamide 2-Iodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl-4-methyl-pyridine (Aldrich, 1.23 g, 6 mmol) in CH2Cl2 (10 mL)at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3*10 mL). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70percent). 1H NMR (300 MHz, CD3OD) delta 7.07-7.12 (m, 1H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1H) ppm. MS (DCI): m/z 316 (M+H)+.
  • 4
  • [ 29835-28-7 ]
  • [ 143321-89-5 ]
  • [ 93716-78-0 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate; L-proline; copper(I) bromide; In dimethyl sulfoxide; at 100℃; for 3h;Inert atmosphere; General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.
 

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