A selective synthesis of 4‐bromo‐2‐furancarboxaldehyde and its pinacolborane derivative | Zendy

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A selective synthesis of 4‐bromo‐2‐furancarboxaldehyde and its pinacolborane derivative

Author(s) -

Ilovich Ohad,

Deutsch Joseph

Publication year - 2005

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570420723

Subject(s) - chemistry , acetal , moiety , reagent , ethylene , methylene , chloride , derivative (finance) , organic chemistry , catalysis , financial economics , economics

A selective synthesis of ethylene acetal of 4‐bromo‐2‐furancarboxaldehyde ( 4 ) and its pinacolborane derivative ( 5 ) is described. The synthesis was carried out using 2‐furancarboxaldehyde ( 1 ) that was bromi‐nated to 4,5‐dibromo‐2‐furancarboxaldehyde ( 2 ) in an emulsion of aluminum chloride and methylene chloride. The product was isolated, protected as ethylene acetal, and selectively debrominated to the ethylene acetal of 4‐bromo‐2‐furancarboxaldehyde ( 4 ) in one step. This moiety was reacted with pinacolborane to give a reactive reagent of Suzuki coupling.

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