Bromoacetanilides

Substances suitable for the estimation acetanilide, sucrose, glucose, cinnamic acid, diphenyl amine, salicylic acid, vanillin, />"bromoacetanilide, toluene p-sul phonamide. 

Mono-substitution products of primary amines cannot easUy be prepared by direct action of the appropriate reagent for example, bromination of aniline yields largely the 2 4 6-tribomo derivative and nitration results in much oxidation. If, however, the amino group is protected as in acetanilide, smooth substitution occurs. Thus with bromine, />-bromoacetanilide is the main product the small quantity of the ortlio isomeride simultaneously formed can be easily eliminated by crystallisation. Hydrolysis of p-bromoacetanilide gives/ -bromoaniline ... 

Baeyer s investigation of indigotin spanned a period of almost 20 years. In 1905, he received the Nobel Prize in recognition of his accomphshments. In 1890, it was observed that treatment of CO-bromoacetanilide with alkali produced oxindole [S9-48-3] (122) (37) ... 

Bromoacetanilide [103-88-8] M 214.1, m 167 . Crystd from aq MeOH or EtOH. Purified by zone refining. 

Bromine acetate has also been proposed310 as an intermediate species in the bromination of anisole, phenetole, and methyl p-tolyl ether by 2,4,6-tribromo-N-bromoacetanilide in acetic acid at 25 °C, since this latter compound was stable to both the ethers and to acetic acid, but in the presence of both, bromination of the ethers occurred, presumably via bromine acetate formed as in the equilibrium... 

A related Heck reaction of substituted o-bromoacetanilides with styrenes followed by selenium-induced cyclization of the resulting o-styiylacetanilides gives 2-arylindoles [378], Substituted o-bromonitrobenzenes react with ethyl vinyl ether under the influence of Pd(OAc)2 to give the corresponding o-ethoxyethenylnitrobenzenes. Zinc reduction then yields indoles [379]. The one-step Pd-catalyzed conversion of o-bromoanilines to indoles 302 with enamines (or with A/-vinyl-2-pyrrolidone) has been reported [380]. 

TMBA-ClBr2 (l.4l g, 4.08 mmol) is added to the acetanilides (3.7 mmol) in CH2Cl2 (50 ml) and MeOH (20 ml) and the mixture is stirred at room temperature until the solution is colourless (ca. 20 min). The solvent is evaporated and the residue is taken up in H20 (20 ml), which is extracted with Et20 (4 x 40 ml). The dried (MgS04) extracts are evaporated to yield the bromoacetanilide. 

Thienyl tellurolates also remove several different substituents such as acetoxy, mesyloxy, phenylthio and 2-thienyltelluro groups, as well as effect the reductive dehalo-genation of bromoacetanilide, and of a-haloacids (such as a-bromophenylacetic acid, a-bromo-l-naphthylacetic acid and a-chlorodiphenylacetic acid). ... 

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