Abstract
A novel synthetic route to 3-amino-5-halo-2-iodobenzoates, which are used as versatile starting materials in the synthesis of pharmaceuticals, was developed using commercially available 2-aminobenzoates bearing a suitable halogen atom at the C5 position as the starting material. Synthesis was initiated with the introduction of a nitro group at the C3 position of the appropriate 2-aminobenzoates, forming 2-amino-3-nitrobenzoates with a C5-halogen atom. The subsequent conversion of the C2-amino group to an iodide yielded 5-halo-2-iodo-3-nitrobenzoates, which were further converted into the desired 3-amino-5-halo-2-iodobenzoates by reducing the C3-nitro group to an amino group. It is worth noting that this transformation can be conducted on a 50 mmol scale, and the desired benzoate compounds were obtained in good yield, demonstrating the practical applicability of this protocol.
Original language | English |
---|---|
Article number | e202400027 |
Journal | Asian Journal of Organic Chemistry |
Volume | 13 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2024 May |
Bibliographical note
Publisher Copyright:© 2024 Wiley-VCH GmbH.
Keywords
- 1,2,3,5-tetrasubstituted benzenoid
- 3-amino-5-halo-2-iodobenzoates
- Sandmeyer reaction
- nitration
- starting material synthesis
ASJC Scopus subject areas
- Organic Chemistry