Synthesis of Ethyl Arylacetates by Means of Friedel-Crafts Reaction of Aromatic Compounds with Ethyl α-Chloro-α-(methylthio)acetate
Friedel-Crafts reaction of aromatic compounds with ethyl α-chloro-α-(methylthio)acetate (1) gave ethyl α-(methylthio)arylacetates (2), which were readily converted into ethyl arylacetates (3) by reductive desulfurization with Raney nickel or zinc dust-acetic acid.The reactions were applied to the syntheses of ibufenac (5) and alclofenac (6), which are anti-inflammatory agents.
Tamura, Yasumitsu,Choi, Hong Dae,Shindo, Hirohisa,Ishibashi, Hiroyuki
p. 915 - 921
(2007/10/02)
ELECTROPHILIC AROMATIC SUBSTITUTION BY PUMMERER REACTION OF α-SULFINYLACETATE
Treatment of a mixture of aromatic compound and ethyl α-(methylsulfinyl)acetate (5) with p-toluenesulfonic acid under continuous removal of separated water brought about an intermolecular aromatic substitution to give ethyl α-(methylthio)arylacetate (6).S
Tamura, Y.,Choi, H.-D.,Shindo, H.,Uenishi, J.,Ishibashi, H.
p. 81 - 84
(2007/10/02)
Introduction of α-(acyl) methylthiomethyl group into the aromatic ring by Friedel-Crafts reaction
Friedel-Crafts α-(acyl)methylthiomethylations of aromatic compounds with α-ethoxycarbonyl, -acetyl, -benzoyl, and -cyano-α-(methylthio)methyl chlorides are described. The resulted products are easily converted to acylmethylated aromatics such as phenylacetate and phenylacetone by reductive desulfurization.
Tamura,Shindo,Uenishi,Ishibashi
p. 2547 - 2548
(2007/10/02)
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