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CAS No. : | 625-99-0 | MDL No. : | MFCD00001046 |
Formula : | C6H4ClI | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JMLWXCJXOYDXRN-UHFFFAOYSA-N |
M.W : | 238.45 | Pubchem ID : | 12269 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
>= 99% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; at 20℃;Inert atmosphere; | General procedure: A round-bottomed flask containing a magentic stirbar and iodobenzene (911.5 mg, 4.468 mmol,1.0 equiv) was added with PdCl2(PPh3)2 (62.9 mg, 0.0896 mmol, 0.02 equiv), CuI (34.9 mg, 0.183mmol, 0.04 equiv) and 5.0 mL of Et3N. The resulted mixture was thoroughly degassed by a steadystream of argon for 15 min before propargyl alcohol (0.14 mL, 270.2 mg, 4.820 mmol, 1.1 equiv)was added via syringe. Ther resulted reaction mixture was allowed to stir at room temperatureunder argon overnight. The reaction mixture was diluted with saturated aqueous NH4Cl and theseparated aqueous layer was extracted with 3xEtOAc. Combined organic phases were washed withsaturated aqueous NaCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to givea crude material. The crude material was purified by SiO2 column chromatography eluting with10% EtOAc-hexane to give the desired product 1a as a brown oil (451.5 mg, 76%);. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; 2,2,6,6-tetramethylheptane-3,5-dione; at 120℃; for 72h; | Step 1 Methyl 1 -(3 -chlorophenyl)- 1 H- indole-7-carboxylate; A mixture of methyl lH-indole-7-carboxylate (0.175 g), 3-iodo-chlorobenzene (0.358 g), Cs2CO3 (0.490 g), CuCl (0.099 g), and 2,2,6,6-tetramethyl-3,5-heptanedione (0.04 mL) in 5 mL of N-methylpyrolidine was heated at 120 0C for 3 days. The mixture was then diluted with 50 mL of EtOAc and filtered through a pad of solica gel. The filtrate was washed with 3 x 15 mL of water and dried over Na2SO4. After filtration and concentration, the residue was purified by Combiflash eluted with a gradient of EtOAc/hexane to give 0.1 g of the title compound.IH NMR (500 MHz, Acetone-d6): delta 7.90 (d, IH), 7.58 (d, IH), 7.50-7.58 (m, 2H), 7.41-7.46 (m, 2H), 7.23 (d, IH), 7.25 (t, IH), 6.83 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99%Chromat. | With palladium diacetate; potassium carbonate; at 100℃; under 5250.53 Torr; for 3h;Catalytic behavior; | General procedure: In a typical experiment, the catalyst precursor (Pd(OAc)2, if otherwise not stated: 0.280mg, 0.00125mmol), 0.5mmol of iodoaromatic compounds, 0.625mmol (1.5 equiv.) of O-nucleophile were dissolved in 2.5mL of solvent followed by addition of 1.25mmol (2.5 equiv.) of base. The reaction mixture was placed in a glass inlet tube into a 25mL Parr Hastelloy-C high-pressure reactor equipped with manometer, safety relief, thermometer and a magnetic stirrer. The reactor was flushed with 10bar of CO three times and placed into a pre-heated oil bath at the given temperature. The final pressure was adjusted at the elevated temperature. The reaction mixture was then stirred for 4h. The pressure was monitored and maintained throughout the reaction. After cooling and venting of the autoclave after a given reaction time, the solution was removed and immediately analyzed by GC-FID and/or GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.5% | With potassium phosphate; silver(I) acetate; palladium diacetate; trifluoroacetic acid; In 1,2-dichloro-ethane; at 80 - 90℃; | Example 43-chloro -2 the same-acetamido [...] synthesis ofTo 10 ml reaction flask by adding 3-bromo(acetylaniline) (0.2mmol, 42 . 81 mg), palladium acetate (0.002mmol, 0 . 45 mg), 3- chloroiodobenzene (0.22mmol, 52 . 46 mg), K3PO4(0.6mmol, 127 . 36 mg), silver acetate (0.3mmol, 50 . 07 mg), TFA (0.1mmol) and DCE (2 ml), for 90 C reaction under the conditions, the TLC reaction monitoring, when the temperature is reduced to the room temperature, adding phenylo boric acid (1.2mmol, 29 . 26 mg) with the ligand two phenol (0.004mmol, 1 . 07 mg), 80 C to continue reaction, the end point of the detection reaction TLC. When the reaction to room temperature, add 5 ml ethyl ether, the reaction solution is poured into the separatory funnel, using 5 ml ethyl ether washing reaction bottle, and then merged into the separatory funnel in ethyl ether, is added to the separatory funnel in 10 ml saturated NaCl solution, oscillating, liquid, so then to 10 ml × 2 of ethyl ether extraction, combined with the phase, adding anhydrous sodium sulfate for drying, filtering, vacuum screwed out of the solvent, with petroleum ether and ethyl acetate 3:1(v/v) as the mobile phase, rapid column separation, get the pure product white solid 3-chloro -2 the three-acetamido [...] biphenyl, yield 86.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h; | General procedure: A solution of <strong>[57090-88-7]4-cyano-1H-imidazole</strong> (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield). |