Manufacturing synthesis of 5-substituted phthalides

F. Faigl, Angelika Thurner, Balázs Molnár, Gyula Simig, Balázs Volk

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.

Original languageEnglish
Pages (from-to)617-622
Number of pages6
JournalOrganic Process Research and Development
Volume14
Issue number3
DOIs
Publication statusPublished - May 21 2010

Fingerprint

manufacturing
synthesis
rings
Dimethylformamide
closures
analogs
phthalide

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Manufacturing synthesis of 5-substituted phthalides. / Faigl, F.; Thurner, Angelika; Molnár, Balázs; Simig, Gyula; Volk, Balázs.

In: Organic Process Research and Development, Vol. 14, No. 3, 21.05.2010, p. 617-622.

Research output: Contribution to journalArticle

Faigl, F. ; Thurner, Angelika ; Molnár, Balázs ; Simig, Gyula ; Volk, Balázs. / Manufacturing synthesis of 5-substituted phthalides. In: Organic Process Research and Development. 2010 ; Vol. 14, No. 3. pp. 617-622.
@article{5810a81b23a745379a824faaaf818514,
title = "Manufacturing synthesis of 5-substituted phthalides",
abstract = "A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.",
author = "F. Faigl and Angelika Thurner and Bal{\'a}zs Moln{\'a}r and Gyula Simig and Bal{\'a}zs Volk",
year = "2010",
month = "5",
day = "21",
doi = "10.1021/op100049t",
language = "English",
volume = "14",
pages = "617--622",
journal = "Organic Process Research and Development",
issn = "1083-6160",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - Manufacturing synthesis of 5-substituted phthalides

AU - Faigl, F.

AU - Thurner, Angelika

AU - Molnár, Balázs

AU - Simig, Gyula

AU - Volk, Balázs

PY - 2010/5/21

Y1 - 2010/5/21

N2 - A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.

AB - A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.

UR - http://www.scopus.com/inward/record.url?scp=77952919515&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77952919515&partnerID=8YFLogxK

U2 - 10.1021/op100049t

DO - 10.1021/op100049t

M3 - Article

VL - 14

SP - 617

EP - 622

JO - Organic Process Research and Development

JF - Organic Process Research and Development

SN - 1083-6160

IS - 3

ER -