Production of formyl-phenylboronic acid compounds, useful as, e.g. enzyme stabilizers, bactericidal agents or in synthesis of pharmaceuticals, comprises reacting protected chlorobenzaldehyde with lithium and boron compound

摘要

Production of formyl-phenylboronic acids (I), comprises: (A) reacting protected chlorobenzaldehyde (acetal, oxazolidine or aminal derivatives) with lithium in inert solvent; and (B) reacting the resulting aryl-lithium compound with a suitable boron compound, e.g. boron trihalide or trialkyl borate. Production of formyl-phenylboronic acids of formula (I), comprises: (A) reacting protected chlorobenzaldehyde of formula (II) with lithium in inert solvent; and (B) reacting the resulting aryl-lithium compound of formula (III) with a suitable boron compound of formula BY3. Y = halo, 1-6C alkoxy, 1-6C alkylthio or 1-5C dialkylamino; R = H, 1-5C alkyl or 1-5C alkoxy; CHX2 = group of formula (IV) - (VII); R<1>-R<4> = H, 1-12C alkyl or phenyl;or R<1>+R<2> or R<1>+R<3> = 5- or 6-membered aliphatic or aromatic ring; and R<5>, R' = 1-6C alkyl or aryl.