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Facile Synthesis of 3‐(ω‐Haloalkyl)thiophenes as Key Building Blocks for Functionalized Thiophenes and Polythiophenes
Author(s) -
Bäuerle Peter,
Würthner Frank,
Heid Stephan
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199004191
Subject(s) - alkyl , chemistry , halide , yield (engineering) , ether , acetic anhydride , reagent , acetic acid , grignard reaction , thiophene , organic chemistry , cleavage (geology) , grignard reagent , catalysis , medicinal chemistry , combinatorial chemistry , materials science , metallurgy , fracture (geology) , composite material
3‐[ω‐( p ‐Methoxyphenoxy)alkyl]thiophenes 2 have become accessible via the Grignard reagents derived from the corresponding alkyl halides, since these undergo nickel‐catalyzed Grignard coupling with 3‐bromothiophene 1 . Ether cleavage with hydrohalic acid/acetic anhydride leads in good yield (51–76%) to the 3‐(ω‐haloalkyl)thiophenes 3 , Hal Br or I, with variable chain length n ≥ 4. These substances are in turn key intermediates in the synthesis of functionalized thiophenes and polythiophenes.