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CAS No. : | 86-55-5 | MDL No. : | MFCD00004007 |
Formula : | C11H8O2 | Boiling Point : | - |
Linear Structure Formula : | C10H7(COOH) | InChI Key : | LNETULKMXZVUST-UHFFFAOYSA-N |
M.W : | 172.18 | Pubchem ID : | 6847 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
86% | With caesium carbonate;silica gel; In dichloromethane; ethyl acetate; toluene; | EXAMPLE 18 Synthesis of 4-Phenoxybenzonitrile 4-Bromobenzonitrile (2.5 mmol), phenol (3.5 or 5.0 mmol), Cs2CO3 (3.5 or 5.0 mmol), (CuOTf)2 PhH (0.0625 mmol, 5.0 mol % Cu), ethyl acetate (0.125 mmol, 5.0 mol %), 1-naphthoic acid (3.5 mmol), molecular sieves (625 mg) and toluene (1.5 mL) were added to an oven-dried test tube which was then sealed with a septum, purged with argon, and heated to 110 C under argon until the aryl halide was consumed as determined by GC analysis. Upon cooling at room temperature, dichloromethane was added and the solvent was removed by filtration. The remaining molecular sieves were stirred with another portion of dichloromethane for 1 h at room temperature, and the solvent was removed by filtration. The combined organic phases were washed with 5% aqueous NaOH. The aqueous layer was then extracted three times with dichloromethane and the combined organic layers were washed with brine. The organic layer was dried over Mg2SO4 and concentrated under vacuum to give the crude product. Purification by flash column chromatography (3% EtOAc/hexane) gave the analytically pure product as a clear oil (405 mg, 86% yield). 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=8.7 Hz, 2H), 7.40 (t, J=7.9Hz, 2H), 7.22 (t, J=7.6Hz, 1H), 7.05 (d, J=7.9Hz, 2H), 6.98 (d, J=8.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 154.6, 133.9, 130.0, 124.9, 120.2, 118.6, 117.7, 105.6; IR (neat): 3068, 2226, 1586, 1483, 1245, 1165 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With di-isopropyl azodicarboxylate; 5,15,10,20-tetraphenylporphyrin; In tetrahydrofuran; ethyl acetate;Inert atmosphere; | To a stirred solution of sugar key intermediate 1a (1.0 equiv) and 1-naphthoic acid (2.0 equiv) in THF was added TPP (2.5 equiv) in one lot at RT. Cooled the reaction mixture to 10-15 C and DIAD (2.75 equiv) was added drop wise at the same temperature under argon atmosphere.The progress of reaction was monitored by TLC and LCMS. After completion of the reaction, reaction mixture was concentrated completely to obtain crude compound, which was purified through column chromatography using silica gel (100-200 mesh), elution gradient 0-12% ethyl acetate in pet-ether. The collected pure fractions were concentrated to obtain desired compound which was used for the next step. |
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