Bromides acids

The 1-silylpentylmetal species thus formed could react with allyl bromide, propargyl bromide, acid chlorides and a,/3-unsaturated ketones (Scheme 14). 

In the presence of a small amount of bromide, acidic bromate oxidations are autocatalytic, and several oxybromo species are present in the reaction mixture,36 according to Eqs. (20)-(22). 

As a synthetic approach this reaction is valuable for the generation of acid bromides, acid iodides and acid fluorides. The readily accessible acid chlorides are a convenient starting material. Thus, it is possible to react acid chlorides with hydrogen fluoride, hydrogen bromide or hydrogen iodide to obtain the corresponding acid halides. ... 

Bradsher and co-workers have developed a general method for synthesizing the protoberberine ring system. It involves the condensation of a properly constituted 1-isoquinoline carboxaldehyde with the appropriately substituted benzyl bromide. Acid-catalyzed cyclization of the resulting quaternary salts affords the fully aromatic tetracyclic ring system which on catalytic reduction leads directly to the tetrahydro-protoberberine skeleton. Recent modifications 93) of this synthetic method involving the use of the oxime, or better, the ethylene acetal of the 1-isoquinoline carboxaldehyde, have permitted the use of less vigorous conditions for the production of the tetracyclic intermediate... 

The synthesis of (2 5, 6R, 8 S)-2,8-dimethyl-l,7-dioxaspiro[5,5]undecane (868), one of the spiroacetal components of the pheromone isolated from the olive fruit fly, hinges on a dialkylation of tolylmethyl isocyanide with bromide 866. The bromide is obtained from 845b by sequential reduction of the olefin and ester followed by conversion of the resulting alcohol to bromide. Acidic hydrolysis of dialkylated product 867 provides the pheromone 868 directly... 

Benzylic and allylic chlorides and bromides, acid chlorides and bromides, and a-haloketones, a-haloesters, a-haloamides, and a-halonitriles also give a positive test at room temperature. 

In contrast to the alkynylation of acidic C-H bonds which can also be achieved using alkynyliodonium salts, the direct C-H functionalization of aromatic compounds or olefins has never been realized with this class of reagents so far. However, after several unsuccessful attempts using palladium or copper catalysts and alkynyliodonium salts for the alkynylation of heterocycles, Waser and Brand reported in 2009 the first efficient alkynylation of indoles using TIPS-EBX 52 and AuCl as catalyst (Scheme 18) [117]. With indole, selective C3-aIkynylation was obtained. The reaction was tolerant to many functional groups such as bromides, acids, or alcohols. The method was already used in the synthesis of starting materials for Friedel-Crafts reactions of aminocyclopropanes [118] and for hydroamidation to access indole c -enamides [119]. In 2010, Nevado and de Haro demonstrated that alkynylation was also possible using directly terminal propiolic ester derivatives and (diacetoxyiodo)benzene as co-oxidant [120]. 

Reacting substances alkyl chlorides and bromides, acid chlorides and bromides, allyl chlorides and bromides, ketones, esters, amides and nitriles substituted with chlorine or bromine in a-position. For discussion see p. 136. 

Meyer JD, Reid EE (1933) Isomorphism and alternation in the melting points of the normal alcohols, acetates, bromides, acids and ethylesters from Cm to C19. J Am Chem Soc... 

Functionalized boronic esters can be alternatively prepared from readily available iodoaryl boronic esters such as 17 and 18.1/Mg-exchange with i-PrMgCl- LiCl provides a bimetallic B/Mg-species such as 19 and 20 that react with a range of electrophiles (aldehyde, allyl bromide, acid chloride, 3-iodo-2[Pg.48]

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