Phenylmagnesium bromide 4- chloro

More conclusive evidence for the intermediacy of benzocyclopropenyl cations was obtained upon chloride/fluoride exchange of 22 with AgF in acetonitrile, which led to the chloro-fluoro derivative 278 and, ultimately, to the difluoro compound 279 in almost quantitative yield. Reaction of 22 with LiAlH AlClj afforded 2,5-diphenylbenzocyclopropene (264), while that with ethyl magnesium bromide lead to the diethyl derivative 280. Phenylmagnesium bromide and methylmagne-... 

A)-Pinanediol ethylboronate with (l,l-dichloroelhyl)lithium yields the (S)-a-chloro boronic ester (89 11 d.r.), which is converted by phenylmagnesium bromide to the (S)-tert-alkylboronate, the same isomer obtained from (S )-pinanediol phenylboronate. The enantiomeric excess of the derived (R)-2-phenyl-2-butanol is 70%. 

Reaction of silicon tetrafluoride with phenylmagnesium bromide at 0 C in diethyl ether provides fluorotriphenylsilane and fluorodiphenylsilane in 59.5 and 5% yield, respectively.3 Chloro(cy-clohexyl)(l-naphthyl)silane is converted into (cyclohexyl)fluoro(l-naphthyl)silane by reaction with a reagent which is prepared by bubbling silicon tetrafluoride through a mixture of tet-rahydrofuran and water.12... 

Trifluorovinylmagncsium iodide couples with chloro(diethoxy)phosphanc to give the trifluoro-vinylphosphane 32 in moderate yield and phenylbis(trifluoromethyl)phosphane (34) can be obtained by reacting chlorbis(trifluoromethyl)phosphanc (33) with phenylmagnesium bromide. ... 

Chloropyrazine 1-oxide with phenylmagnesium bromide in tetrahydrofuran at reflux gave 2-chloro-6-phenylpyrazine 1-oxide (733b). 

Formation of 1,3,5-triazine derivatives has also been observed in the reaction of 3-halo-5-phenyl-1,2,4-triazines with potassium amide in liquid ammonia (80JOC881) and on treatment of 3-chloro-5,6-diphenyl-l,2,4-tri-azine with phenylmagnesium bromide (83IJC(B)559). Both transformations were assumed to be initiated by the addition of the nucleophile employed at C-5 of the 1,2,4-triazine ring. 

Reaction of 3-chloro-5,6-diphenyl-l,2,4-triazine with phenylmagnesium bromide has been found to result in a rather complex mixture of 12 products ), including tetraphenylimidazole (169) and triphenylimidazolone 172. 2,5-Dihydro-1,2,4-triazines 168 and 171, resulting from the addition of the Grignard reagent at C-5 of 3,5,6-triphenyl-l,2,4-triazine 167 and 5,6-diphenyl-l,2,4-triazin-3-one 170, are postulated as the key intermedi-... 

The reaction of 3,5-dichloro-A,A-diisopropyl-1 /.4,2,4,6-thiatriazin-l -amine (2) with butyllithi-um gives only dibutyl ketone, probably formed from the ring-transformation product benzoni-trile via butyllithium addition to the ketone imine.45 Reaction of phenylmagnesium bromide with 2 gives 3-chloro-Al,Af-diisopropyl-5-phenyl-lA4,2,4,6-thiatriazin-l-amine (3) in 30% yield.45... 

The reaction of chloroformamidines with phenylmagnesium bromide results in the replacement of the chloro group by a phenyl group... 

Step conversion. A slight excess of ethereal phenylmagnesium bromide added to a soln. of 3,4-dichloro-6-methylcoumarin in benzene 3-chloro-6-methyl-flavone. Y 70%. M. S. Newman and J. L. Ferrari, Tetrah. Let. 1962, 199. 

Preparative Methods can be prepared either by the reaction of phenylmagnesium bromide with chloro(chloromethyl)di-methylsilane in ether at reflux, or by the reaction of phenylmagnesium bromide with chloro(chloromethyl)dimethylsilane in the presence of catalytic (Al,Al,lY,iV -tetramethylethylenedi-amine)zinc in 1,4-dioxane at 20 °C ... 

In an argon-flushed, 25-mL Schlenk flask with a septum, Pd(OAc)2 (0.0180 mg, 0.080 mmol) and PCyj (0.0224 mg, 0.080 mmol) are dissolved in dry A methyl-2-pyrrolidone (NMP) (5 mL). 3-Chloro-l,l-diethoxypropane (78 0.33 g, 2 mmol) is added by syringe, followed by a dropwise addition of phenylmagnesium bromide (3 mL, 1 M in THF, 3 mmol) over 1 min in order to keep the reaction temperature below 40 C. The reaction mixture is stirred 20 h at 25 °C and then quenched with MeOH (1 mL) and water (1 mL). Removal of the solvent and purification by column chromatography (heptanes) gives (3,3-diethoxy-propyl)-benzene (79 74% yield). ... 

Metalation. Benzene reacts with alkali metal derivatives such as methyl or ethyUithium in hydrocarbon solvents to produce phenyllithium [591-51-5], C6H5Li, and methane or ethane. Chloro-, bromo-, or iodobenzene will react with magnesium metal in ethereal solvents to produce phenylmagnesium chloride [100-59-4], C6H5MgCl, bromide, or iodide (Grignard reagents) (32). 

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