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Regioselective Preparation of 3‐Alkoxy‐4,5‐difluoroanilines by S N Ar
Author(s) -
Van Brandt Sven,
Rombouts Frederik J. R.,
MartínezLamenca Carolina,
Leenaerts Jos,
Rauws Tom R. M.,
Trabanco Andrés A.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201228
Subject(s) - chemistry , regioselectivity , electrophile , nucleophile , alkoxy group , toluene , catalysis , base (topology) , organic chemistry , combinatorial chemistry , alkyl , mathematical analysis , mathematics
A simple and scalable procedure to introduce alcohols selectively at the 3‐position of 3,4,5‐trifluoroaniline is described. The procedure uses powdered NaOH as base and catalytic 15‐crown‐5 in refluxing toluene with a Dean–Stark trap. A short exploration of other nucleophiles and fluoroaryl electrophiles is also described.