3-methyl-5-phenyl- -bromide

Selenonium Carboxymethyl-methyl-(4-methyl-phenyl)- (bromid) IX, 1039... 

Arsoninm Diallyl-methyl-phenyl-(bromid) XIII/8, 403... 

Scheme 15.1. Suzuki coupling of phenyl boronic acid with 4-methyl phenyl bromide.

Deall lation. Chloroformates such as vinyl chloroformates (40) are used to dealkylate tertiary amines. Chloroformates are superior to the typical Von Braun reagent, cyanogen bromide, because of increased selectivity producing cleaner products. Other chloroformates such as aHyl, methyl, phenyl, and trichloroethyl have also been used in dealkylation reactions. Although the dealkylation reaction using chloroformates is mostiy carried out on tertiary amines, dealkylation of oxygen or sulfur centers, ie, ethers or thioethers, can also be achieved. a-Chloroethyl chloroformate [50893-53-3] (ACE-Cl) (41,42) is superior to all previously used chloroformates for the dealkylation reaction. ACE-Cl has the advantage that the conditions requked for ACE... 

Acetophenone Methyl phenyl ketone 1.34 CgHgO Hydrogen bromide 226 HBr... 

TABLE 23. Reductive cleavage of benzylmethylphenyl-n-propylphosphonium bromide to methyl-phenyl-n-propylphosphine... 

When the ethylene oxide contains an aromatic substituent, as in styrene oxide, there is a significant tendency for preliminary isomerization to oocur. Thus, treatment of styrene oxide with methyl-magnesium bromide or ethylmagnesium bromide yields 1 -phenyl-2-propauol and l-phemyJ-2-butanol respectively1 83 (Eq. 841). 

The Grignard reagent—magnesium phenyl bromide—is prepared as described in Preparation 21 from 1-2 gms. (1 mol.) of dry magnesium and 8 gms. (1 mol.) of dry bromobenzene. 6-8 gms. (1 mol.) of dry methyl benzoate dissolved in 25 gms. of sodium-dried ether are added to the cold solution, slowly and with constant shaking. The liquid is then heated on a water bath until no further change takes place. Ice and dilute sulphuric acid are added to the cold reaction mixture, which, when the precipitate has dissolved, is steam distilled. The triphenyl carbinol which remains is recrystallised from benzene. 

When A.A-dimethylisoindolinium bromide is treated with phenyl-lithium, it gives V-methylisoindole via the ylid (54).2 59,60 An attempt to prepare benzo[c]thiophene via the analogous ylid (55) failed. Thus, when l,3-dihydrobenzo[c]thiophene methylsulfonium iodide was treated with phenyllithium, it gave a mixture of methyl phenyl sulfide, spiro[5.5]-l-methylthio-2,3-benzo-6-methylthio-methyleneundeca-7,9-diene (56), and 3,4-bis(methylthio)-l,2 5,6-dibenzo-l,5-cyclooctadiene (57).59,60 The formation of methyl phenyl sulfide may be explained by the formation and ring cleavage of compound 58, and compounds 56 and 57 arise by Diels-Alder dimerization of the o-quinodimethane (59) formed by ring cleavage of the ylid (55). 

Cyclization of l-(2-phenyl-2-oxoethyl)-2-[phenyl(hydroxyimino)-methyl]pyridinium bromide (288) in boiling 48% HBr for 10 minutes gave 3-hydroxy-l, 3-diphenyl-3,4-dihydropyrido[l, 2-a]pyrazinium bromide (289) (Scheme 11). When the reaction period was 6 h, 1,3-diphenylpyrido-... 

Brom-cthyl)-ethyl- E2, 125 (4-Brom-a-hydroxy-benzyl)-phenyl- E2, 128 Brommethyl-methyl-j -bromid E2, 155 (4-Brom-phenyl)-(l-ethoxycarbonyl-l-hydroxy-ethyl)- E2, 128... 

When tellurium dioxide, lithium bromide, and the semicarbazone of methyl phenyl ketone reacted in acetic acid, 6-bromobenzotellurophene was isolated in 9% yield1. 

Treatment of enantiomerically pure cyclic sulfonimidates 6 and 7 with allyllithium or allylmagnesium bromide gives optically active allylic sulfoximines 8 and 9 (R = allyl) as described in Section II.A.13 The reactions of /V-phenyl-S-(methyl-phenyl)sulfoximidoyl chloride 109 with allyltrimethylsilane or allyltributylstan-... 

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