Phenylmagnesium bromide 4-methoxy

Alteration of the relative reactivity of the ring-positions of quinoline is expected and observed when cyclic transition states can intervene. Quinoline plus phenylmagnesium bromide (Et20,150°, 3 hr) produces the 2-phenyl derivative (66% yield) phenyllithium gives predominantly the same product along with a little of the 4-phenylation product. Reaction of butyllithium (Et 0, —35°, 15 min) forms 2-butylquinoline directly in 94% yield. 2-Aryl- or 6-methoxy-quinolines give addition at the 2-position with aryllithium re-agents, and reaction there is so favored that appreciable substitution (35%) takes place at the 2-position even in the 4-chloroquinoline 414. Hydride reduction at the 2-position of quinoline predominates. Reaction of amide ion at the 2-position via a cyclic... 

Diphenylbenzo[( ]furan has been observed in a number of other reactions. When benzocyclobutadienequinone (172), monothiophthalic anhydride (173), chlorophthalide (the chloride of o-phthalaldehydic acid, 174),and 2-cyanobenzaldehyde (175) are treated with phenylmagne-sium bromide, 138 could be obtained. This last reaction, which yields an imine in the primary stage, has also been conducted with p-methoxy-phenylmagnesium bromide. ... 

Dibromo-l-methoxypropane in turn with phenylmagnesium-bromide gave the product, which after hydrolysis yielded l-phenyl-l-methoxy-2-bromopropane. 

Chiral auxiliaries are particularly important in asymmetric synthesis. A bicyclic orthoester derived from dimethyl-L-tartrate (la) provides a novel auxiliary with useful applications. Treating la with phenylmagnesium bromide followed by reaction with methyl 2-methoxy-2,2-dichloroacetate (commercially available) affords in greater than 75% yield the methyl... 

The Q- and -glycosidic products formed by reaction of tetra-Q-acetyl-a-D-glucopyranosyl chloride with various methoxy-substitutad phenylmagnesium bromides have been examined.That aryl Q-glycosides can rearrange to aryl -glycosides is illustrated in Scheme 21, and likewise the 9-naphthylglycoside CHjOMe... 

Synthetic Transformations of 2-Pyridyl-substituted Vinyl-silane. 2-Pyridyl-substituted vinylsilanes can be converted into other vinylsilanes. Subjection of 2-pyridyl-substituted vinylsi-lanes to potassium fluoride/methanol leads to the formation of methoxy(vinyl)silanes by pyridyl-silyl bond cleavage (eq 4). The resultant methoxysilanes can be further allowed to react with Grig-nard reagents such as phenylmagnesium bromide to give the corresponding vinylsilanes that are commonly used for various transformations (eq 4). ... 

Preparation by adding phenylmagnesium bromide to 2-methoxy-5-(trifluoromethyl)benzonitrile,followed by hydrolysis of the intermediate imino compound formed, then demethylation of 2-methoxy-5-(trifluoromethyl)-benzophenone so obtained [568]. - Preparation by demethylation of 2-methoxy-5-(trifluoromethyl)benzophenone with boron trichloride in methylene chloride at -60° for 1 h, then at r.t. [569]. 

Preparation by demethylation of 2,3-dimethyl-4-methoxy-benzophenone (SM) with pyridin-ium chloride at 180° for 2 h. SM was prepared by reaction of phenylmagnesium bromide with 2,3-dimethyl-4-methoxybenzal-dehyde in ethyl ether at 0° for 30 min [477],... 

Also obtained by reaction of 4-methoxyphenylglyoxylonitrile with 4-methoxy-phenylmagnesium bromide in the presence of Fe(acac)j (5 mol%) in THF at -10° for 30 min under argon (98%) [1525],... 

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