TY - JOUR
T1 - A selective synthesis of 4-bromo-2-furancarboxaldehyde and its pinacolborane derivative
AU - Ilovich, Ohad
AU - Deutsch, Joseph
PY - 2005
Y1 - 2005
N2 - 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 brominated 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.
AB - 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 brominated 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.
UR - http://www.scopus.com/inward/record.url?scp=28244441309&partnerID=8YFLogxK
U2 - 10.1002/jhet.5570420723
DO - 10.1002/jhet.5570420723
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AN - SCOPUS:28244441309
SN - 0022-152X
VL - 42
SP - 1409
EP - 1411
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 7
ER -