2-Methoxyphenyl magnesium bromid

Bis(p-methoxyphenyl) ditelluride (typicalprocedure To a solution of p-methoxyphenyl-magnesium bromide (prepared from p-bromoanisole (5.82 g, 0.0311 mol) and Mg (1.0 g, 0.042 mol) in THF (20 mL)) is added Te shot (3.81 g, 0.0300 mol) at room temperature. The mixture is stirred under reflux for 3 h and then cooled to 0°C and treated with a sam-rated solution of NH Cl (20 mL vigorous evolution of gas). The mixture is filtered through Celite and the solids washed with saturated solution of NH Cl and ether. The organic phase is washed with brine and dried with Na2S04. Evaporation of the solvent and recrystaUiza-tion from CHClj/petroleum ether affords the pure product (5.16 g (75%) m.p. 57-59°C). 

Tris[trimethylsilyl]methyl tellurium iodide reacted with phenylmagnesium bromidebutyl tellurium bromide with vinyl magnesium bromide, vinyl tellurium iodide with butyl and 4-methoxyphenyl magnesium bromide, and 2-propenyl tellurium iodide with 4-methoxyph-enyl magnesium bromide to give the expected unsymmetric dialkyl or alkyl aryl tellurium compounds. 

Obtained by reaction of 4-methoxyphenyl-magnesium bromide with 3-chloro-2-flnoro-N-methoxy-N-methylbenzamide [1761]. 

Abstract. Grignard reactions are of utmost importance in organic synthesis (Lee, 2005), and finding the prime conditions under which to conduct these reactions is really crucial to their usefulness. This work looks at the effects of time, and temperature on yield in the reaction of isopropyl magnesium bromide with 4-methoxyben-zaldehyde to produce l-(4-methoxyphenyl)-2-methylpropan-l-ol. The reaction was first run for 10 min at 25, 50, 75, and 80 °C. Next it was run at 80 °C for 10, 20, and 30 min (see Methods section for more details). Highest yields (85%) were obtained at 80 °C with 10-20 min reaction times. Utilizing conditions that optimize yields will improve the economic practicality of these reactions, and increase their usefulness as a synthetic tool. 

Refluxing 3-chloro-2-acyloxypropyl tellurium trichlorides with Raney nickel in ethanol resulted in the displacement of the trichlorotelluro group by hydrogen. The 3-chloro-2-acyloxypropanes were isolated in yields of approximately 50%4. Aryl tellurium trichlorides, when treated similarly, produced the parent aromatic hydrocarbons and biaryls5. All possible biaryls were formed when 4-methoxyphenyl tellurium trichloride was treated with phenyl magnesium bromide in THF in the presence of the nickel chloride triphenylphosphane adduct6. 

Methoxyphenyl Phenyl Tellurium (Grignard Method) Phenyl magnesium bromide is prepared from 0.84 g (35 mmol) of magnesium and 5.5 g (35 mmol) of bromobenzene in 15 m/ of absolute diethyl ether under nitrogen and the resultant solution is cooled in an ice/watcr bath. 4.7 g (10 mmol) of bis [4-methoxyphenyl] ditellurium dissolved in 100 ml of absolute diethyl ether are added dropwise to the Grignard solution. Then 250 ml of petroleum ether (b.p. 30- 50°) are added to precipitate the tellurolate and the mixture is allowed to stand for 2 h. The precipitate is filtered off, the filtrate is mixed with aqueous ammonium chloride solution, the organic phase is separated, dried with sodium sulfate, and the solvent is evaporated. Methanol is added to the oily residue to crystallize the product yield 3.1 g (100%) m.p. 61° (from methanol). 

Previous preparations by Scolastico were based on the Strecker synthesis of aminonitrile and lacked steroselectivity [74,75]. More recently, two formal syntheses were reported from the same ketone 71. In Rama Rao s synthesis (Scheme 11.19) [76], 71 was condensed with vinyl magnesium bromide to give the tertiary alcohol 72 as a single isomer. This compound was then transformed into the vinyl epoxide 73 that, under palladium catalysis, reacted with 4-methoxyphenyl isocyanate to produce the oxazohdinone 74 with retention of its configuration. The remainder of the synthesis consisted of heterocycle opening and adjustment of the oxidation level to provide the lactone 75. Excision of two carbons was necessary to form the known aldehyde 76, previously transformed into myriocin [74]. 

The allylic alcohol 209 obtained from 3-(m-methoxyphenyl) propanol and isopropenyl magnesium bromide in THE at - 78 C was converted to the ketone 210 by a chloroketal Claisen reaction. ° Reaction with isopropenyllithium followed by reduction of the resulting allylic epoxide (211) resulted in formation of the tetramethyl allylic alcohol 212. Cyclization with stannous chloride" afforded an 85 15 mixture of 213 214 ozonolysis of 213 afforded 215, the route... 

D-Limonene dimercaptan Magnesium bromide Maleic hydrazide, diethanolamine salt , Malononitrile Mandelic acid Melamine 1,8-p-Menthanediamine Mercury chloride (ic) 2-Methoxy-5-nitroaniline 4-p-Methoxyphenyl-2-butanone Methyl acetoacetate Methylal Methylaluminum dichloride Methyl amyl alcohol N-Methylaniline... 

In an attempt to synthesize a thiochalcone by the reaction of 3-(NN-di-ethylamino)-l-(p-methoxyphenyl)propene-l-thione with phenyl magnesium bromide, in an ogy with a well-known synthesis of chalcones, Quiniou and his co-workers obtained instead the thiopyran (88), a formal dimer of the thiochalcone expected." The thiirans (89) were formed by the reaction of... 

Hexestrol Hexestrol, 4,4 -(l,2-diethylethylene)diphenol (28.1.29), is a derivative of a,j3-diphenylethane, and it is a synthetic estrogen. Hexestrol is made in a Wurtz dimerization reaction of l-bromo-l-(4-methoxyphenyl)propane (28.1.27) in the presence of sodium, magnesium, aluminum, or iron. The initial l-bromo-l-(4-methoxyphenyl)propane (28.1.27) is made in turn by addition reaction of hydrogen bromide to 4-methoxy-l-propenylbenzene. Subsequent removal of the methoxy protective groups from the resulting dimerization product (28.1.28) using hydroiodic acid gives hexestrol (28.1.29) [37-43]. 

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