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Details for Patent: 3,759,987

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Details for Patent: 3,759,987

Title: PREPARATION OF 5-FLUORO-2-METHYL-1-(P-METHYLSULFINYLBENZYLIDENE)-3-INDENYL ACETIC ACID
Abstract:Process for preparing 1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acids by introducing a methylsulfinyl group into a 1-benzylidene-3-indenyl acetic acid.
Inventor(s): Conn; John B. (Westfield, NJ), Bollinger; Frederick W. (Westfield, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Filing Date:May 01, 1970
Application Number:05/033,974
Claims:1. A process wherein a compound of the formula: ##SPC8##

wherein E is hydrogen, lower alkyl or quaternary ammonium base, is

a. diazotized to a diazonium compound;

b. said diazonium compound is treated with sulfur dioxide to form a sulfinic acid compound;

c. said sulfinic acid compound is treated with a chlorinating agent to form the corresponding chlorosulfinyl compound;

d. said chlorosulfinyl compound is esterified to form the corresponding ester;

e. said ester is treated with a alkyl magnesium halide followed by addition of an aqueous acid to form the 3-indenyl acetone compound; and

f. converting said 3-indenyl acetone compound to 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acid by the haloform reaction.
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