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In organic chemistry, the Bruylants reaction (sometimes misspelled Bruylant) is a substitution reaction in which a Grignard reagent replaces a nitrile on a carbon that also has an amino group. It is useful for synthesizing phenylcyclidine and related dissociative anesthetics .
Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH 3 and phenylmagnesium bromide (C 6 H 5)−Mg−Br. They are a subclass of the organomagnesium compounds.
A solution of a carbonyl compound is added to a Grignard reagent. (See gallery) An example of a Grignard reaction (R 2 or R 3 could be hydrogen). The Grignard reaction (French:) is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...
The traditional method for generating the aryl Grignard reagent proceeds less predictably: slow, heterogeneous: XC 6 H 4 Br + Mg → XC 6 H 4 MgBr. Furthermore, traditional routes to Grignard reagents has limited functional group compatibility, whereas the Turbo-Grignard method tolerates other halides, some ester groups, and nitriles.
The reaction mechanism [8] of the Bartoli indole synthesis is illustrated below using o-nitrotoluene (1) and propenyl Grignard (2) to form 3,7-dimethylindole (13). The mechanism of the Bartoli indole synthesis. The mechanism begins by the addition of the Grignard reagent (2) onto the nitroarene (1) to form intermediate 3.
Ortho esters can be prepared by the Pinner reaction, in which nitriles react with alcohols in the presence of one equivalent of hydrogen chloride. The reaction proceeds by formation of imido ester hydrochloride: RCN + R ′ OH + HCl → [RC(OR ′)=NH 2] + Cl −. Upon standing in the presence of excess alcohol, this intermediate converts to ...
The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]
Kumada coupling reaction, M = catalyst, usually based on Ni or Pd complexes. In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide.