3-Phenoxytoluene

CLEAR VERY SLIGHTLY YELLOW LIQUID

General procedure: To prepare diaryl ethers using the Ullmann coupling reaction via O-arylation reactions, aryl halide (1 mmol), phenol derivative (1 mmol) and 0.2 g (1.5 mmol) of K2CO3 in DMF (5 mL) were placed into a round-bottom flask containing 0.05 g (0.02 mmol) of the catalyst. The above mixture was refluxed at 110 C for 3 h under vigorous stirring. When the reaction was complete, the reaction mixture was cooled and the solvent was removed under reduced pressure. Then, the mixture was diluted with CH2Cl2 and the catalyst was separated by an external magnet. The filtrate was evaporated on a rotary evaporator and the crude product was purified by column chromatography using ethyl acetate/n-hexane.General procedure: The catalytic O-arylation reactions were conducted in asealed stainless-steel reactor. A phenol (14 mmol), aryl halide(14 mmol), Cs2CO3 (14 mmol), tetrahydrofuran (THF, 10 mL), and the Cu2O/SiC catalyst (10 mg) were placed in the reactor.The reaction was performed under Ar at 150 C for 3 h. Afterthe reaction, the suspension was collected and centrifuged. Thesupernatant was analyzed using gas chromatography-massspectrometry (Bruker SCION SQ 456GC-MS, Germany). Theyields and TOFs were calculated based on the aryl halide usingthe following equations:Yield = Conversion (%) selectivity (%)= (1 - na/nb) x ntp/(ntp + nbp) x 100%TOF = Amount of aryl halides (mol) x conversion (%)x selectivity (%)/(mass of Cu2O/SiC (g) x Cu2O loading (%) xreaction time (h)/M[Cu2O] (g/mol))where na is the moles of aryl halide after reaction, nb is themoles of aryl halide before reaction, ntp is the moles of targetproduct after reaction, and nbp is the moles of byproduct afterreaction.General procedure: all reactions were carried out under air. Aryl halides (1.0 mmol) was treated with phenol (1.0 mmol) in the presence of 0.1 mmol CuI , 0.2 mmol 1-(alpha-aminobenzyl)-2-naphthols and 2.0 equiv K2CO3 in 3 mL DMSO at 120 for 24 h.The progress of the reaction was monitored by GC. After completion of the reaction, the catalyst was filtered easily and the product was extracted with EtOAc, The combined organic layers was dried over MgSO4 for 12 h. The solvent was evaporated under reduced pressure and the desired product purified by flash chromatography on a silica gel column using petroleum ether/ethyl acetate (10:1).General procedure: Experimental procedure for the synthesis of diaryl ether: To a stirred solution of iodo benzene (1.0 mmol) and phenol (1.0 mmol) in dry DMSO (2.0 ml) were added Cu catalyst 1 (0.02 mmol) and KOH (2.0 equiv) and the reaction mixture was heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After being cooled the reaction mixture at room temperature, the precipitated catalyst was separated by simple filtration and filtrate so obtained was diluted with ethyl acetate (10 ml). The organic layer was washed with water and dried over anhydrous Na2SO4. The solvent was evaporated under vacuum to give the crude product, which was purified by column chromatography with hexane as eluent to yield the expected product as yellowish oil. The products were analyzed by GC-MS, IR, 1H & 13C NMR analysis.General procedure: In an oven-dried 50 mL round-bottomed flask with a condenser, phenol (1.0 mmol), bromobenzene (1.2 mmol), Cs2CO3 (1.0 mmol) and Cu2O/Cu-CNTs catalyst (0.06 g) were addedunder nitrogen atmosphere, followed by addition of DMSO (10 mL). The reaction mixture washeated in an oil bath at 140 and stirred at this temperature for 24 h. After the completion of thereaction (monitored by TLC), the reaction mixture was filtered. The filtrate was extracted withethyl acetate (3×10 mL) by adding a small amount of saturated aqueous NaCl solution. Theorganic layer was dried with anhydrous MgSO4 and concentrated to get the crude product. Theresulting residue was purified by column chromatography on silica gel to provide the desiredproduct.

Molecular Weight:184.23
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:184.088815002
Monoisotopic Mass:184.088815002
Topological Polar Surface Area:9.2
Heavy Atom Count:14
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes