Process development and manufacture of potassium 2-fluoro-6-hydroxyphenyltrifluoroborate

The development of a phase-appropriate manufacturing-scale synthesis of potassium 2-fluoro-6-hydroxyphenyltrifluoroborate was achieved. Investigations into improving the yield and robustness indicated that pH of the reaction medium is a critical process parameter. Additional development resulted in...

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 32; pp. 4266 - 4270
Main Authors Pawar, Lokesh, Jayaramaiah, Ramesh, Krishnan, Baburaj, Arunachalampillai, Athimoolam, Chen, Ying, Parsons, Andrew T., Robinson, Jo Anna, Tedrow, Jason S.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.08.2019
Elsevier
Subjects
Boron
Boronic acid
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Suzuki coupling
Trifluoroborate
Suzuki coupling
Boronic acid
Boron
Trifluoroborate
REAGENTS
COUPLING REACTIONS
PROTODEBORONATION
SALTS
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Summary:The development of a phase-appropriate manufacturing-scale synthesis of potassium 2-fluoro-6-hydroxyphenyltrifluoroborate was achieved. Investigations into improving the yield and robustness indicated that pH of the reaction medium is a critical process parameter. Additional development resulted in replacing tartaric acid with citric acid, resulting in improved process robustness and enabling scale-up to >10 kg. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.05.063