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CAS No. : | 866632-57-7 | MDL No. : | MFCD2338250 |
Formula : | C7H3F4IO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 306.00 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
To the solution of 3- (trifluoromethoxy)fluorobenzen(1g, 5.5 mmol) in lOmL THF at -78C, n-BuLi (1.6M, 3.75mL) was added dropwise. The resulting solution was stirred at -78C for 30 min. 12 (2.1g, 8.25 mmol) in THF (5mL) was added. The mixture was warmed to room temperature and then quenched with Na2C03 in saturated Na2S203 (1: 10) (30mL). The crude product was extracted with ether. The ether layer was dried over Na2S04 and filtered through a short silica gel column to give the desired iodide as an oil. ¹H NMR (CDC13): 7.39 (m, 1H), 7.12 (d, J=9.0 Hz, 1H), 7.05 (t, J=6.0 Hz, 1H) MS (ESI): m/e 307 (M+1)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 90℃; for 24h;Inert atmosphere; | Example 43-[5-(2-Fluoro-6-trifluoromethoxy-phenyl)-lH-benzimidazol-2-yl]-l-oxa-2- aza-spiro [4.5] dec-2-ene hydrochloride (Cpd 8)A. 2'-Fluoro-3-nitro-6'-trifluoromethoxy-biphenyl-4-ylamine 2-Fluoro-l-iodo-6-trifluoromethoxybenzene (612 mg, 2.00 mmol, prepared as described in WO2005/097136), <strong>[833486-94-5]4-amino-3-nitrophenylboronic acid pinacol ester</strong> (1.3 eq., 687 mg, 2.60 mmol), and (dppf)PdCl2-DCM (0.05 eq., 81.6 mg, 0.100 mmol) were placed in a 40 mL vial equipped with a magnetic stir bar. The vial was evacuated and backflushed with Ar, and DME (10 mL) and 2M aq Na2COs (4 mL) were added via syringe. The vial was capped tightly and placed in a heating block where the reaction was stirred at 90 0C for 24 h. The reaction was cooled to room temperature, diluted with EtOAc, and washed sequentially with water and brine. The organic extract was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using an 80-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0: 1 to 2:3, v/v over 30 min, yielding 548 mg (87 %) of the desired compound. 1H-NMR (400 MHz, CDCl3) delta: 8.21 (s, IH), 7.30 - 7.47 (m, 2H), 7.18 (d, J = 8.1 Hz, IH), 7.14 (t, J = 8.6 Hz, IH), 6.91 (d, J = 6.6 Hz, IH), 5.37 (br. s., 2H). |