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Friedel-Crafts Acylation and Alkylation Reaction

Friedel-Crafts reactions.jpg   Named Reactions in Organic Synthesis
Reaction category:
Electrophilic aromatic substitution

Other featured reactions:

 

In 1877 C.Friedel and J.M. Crafts reacted amyl chloride with aluminium pieces in benzene and formed amylbenzene. The reaction of alkyl halides with benzene was found to be general and aluminium chloride (AlCl3) was identified as the catalyst. Since this discovery, the substitution of both aromatic and aliphatic compounds with a variety of alkylating agents in the presence of a Lewis acid is known as Friedel-Crafts Alkylation.

Mechanism of the Friedel-Crafts Alkylation

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Before the 1940s, the alkylation of aromatic compounds was the foremost application, but later the alkylation of aliphatic systems also gained in importance. In addition to aluminium chloride, other Lewis acids can also be used: BeCl2, CdCl2, BF3, BBr3, GaCl3, AlBr3, FeCl3, TiCl4, SnCl4, SbCl5, lanthanide trihalides, and alkyl aluminium halides.

Closely related to the Friedel-Crafts Alkylation, the introduction of a keto group into an aromatic or aliphatic compound using an acyl halide or anhydride in the presence of a Lewis acid catalyst is known as the Friedel-Crafts Acylation. Compounds that undergo the Friedel-Crafts Alkylation are, in most cases, also easily acylated.

One drawback of the Friedel-Crafts Acylation reaction is that the Lewis acid catalyst often cannot be recovered once the reaction is complete. However heterogeneous catalysts such as zeolites make this reaction more feasible on an industrial scale.

Below are some of the many hundreds of Alfa Aesar products that can be used in Friedel-Crafts acylation and alkylation reactions.

 

 

Other reaction categories:
Nucleophilic substitution
Heterocycle formation
Transition metal-catalyzed couplings
Oxidation
Reactions involving carbonyl compounds
Reduction reactions NEW!


Some relevant Alfa Aesar products for the Friedel-Crafts reaction:


Aluminum Chloride - the key reagent in Friedel-Crafts chemistry
Other Lewis Acids / Inorganic Halides
Organohalide building blocks
Carbonyl halide building blocks

 
Aluminum Chloride Other Lewis Acids Alkyl Halide Building Blocks Carbonyl Halide Building Blocks
Aluminum chloride, anhydrous, 99.999% (metals basis)
Aluminum chloride, anhydrous, 99.985% (metals basis)
Aluminum chloride, anhydrous, granular, 99%
Aluminum chloride, anhydrous, powder, 99%
Aluminum chloride, anhydrous, Reagent Grade
Aluminum chloride, ultra dry, 99.99% (metals basis)
Aluminum chloride, anhydrous, 95+%
Aluminum chloride, ultra dry, 99.999% (metals basis)
Cadmium chloride, anhydrous, ACS, 99.0% min
Boron trifluoride diethyl etherate, 46.5% BF3 min, packaged under Argon in resealable ChemSeal bottles
Gallium(III) chloride, ultra dry, 99.999% (metals basis)
Aluminum bromide, 98%
Iron(III) chloride, anhydrous, 98%
Titanium(IV) chloride, 99.99% (metals basis)
Tin(IV) chloride, anhydrous, 98% (metals basis)
Antimony(V) chloride, 99%
(1,2-Dibromoethyl)benzene
1-Bromooctane
1,6-Dibromohexane
1-Bromohexadecane
2-Chloropropene
2-Iodopropane
1-Chlorohexadecane
2-Ethylhexyl bromide
2-(Chloroethyl)benzene
1-Iodooctane
1-Chlorobutane
1,2-Dichloroethane
2-Chloro-2-methylbutane
1-Bromohexane
Iodomethane
1-Chlorooctadecane
1-Iodohexadecane
Acetyl chloride
Butyryl chloride
Adipoyl chloride
Trimethylacetyl chloride
Bromoacetyl bromide
2-Chloropropionyl chloride
Methoxyacetyl chloride
Benzoyl chloride
Biphenyl-4-carbonyl chloride
Acryloyl chloride

 

Mechanism of the Friedel-Crafts Acylation

Friedel Crafts acylation mechanism

 

The Friedel-Craft reaction is widely used in organic synthesis; e.g., the total synthesis of the potent cytotoxin tri-O-methyl dynemicin A methyl ester.

Friedel–Crafts reactions have uses in the synthesis of triarylmethane and xanthene dyes and the Friedel–Crafts test for aromatic hydrocarbons where reaction of chloroform with aromatic compounds using an aluminium chloride catalyst gives brightly coloured triarylmethanes is a bench test for aromatic compounds.

Despite being over 140 years since it was discovered this reaction and its associated reactions continue to play a key role in organic synthesis e.g. in the search for HIV treatments the Friedel-Crafts reaction was used to prepare anti-HIV cosalane analogues.



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