75280-09-0

Upstream product

• 4455-14-5 ethyl 2-(methylsulfinyl)acetate 
• 108-90-7 chlorobenzene 
• 145628-18-8 ethyl 2-chloro-2-methylthio-acetate 
• 4455-13-4 methylthioacetic acid ethyl ester 

Downstream Products

• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 

Relevant academic research and scientific papers

MILD REACTION OF PUMMERER REARRANGEMENT PRODUCTS WITH AROMATIC COMPOUNDS IN THE PRESENCE OF LEWIS ACIDS. APPLICATION TO THE PREPARATION OF ARYLMETHYLENE KETONES, ARYLACETOESTERS, AND ARYLACETONITRILES.

Pummerer intermediates generated from precursors (3), (4) and (5) reacted mildly with aromatic compounds in the presence of Lewis acids to give the corresponding sulfides which in turn desulfurized to arylmethylene ketones, arylacetoesters, and arylaceton

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.

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

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.