Method for fluoromethylation of alcohols via halogenative decarboxylation
US6271422A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jun 1, 2000 |
| Grant date | Aug 7, 2001 |
| Priority date | — |
| Expiry date | Jun 1, 2020 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C41/22
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A method for fluoromethylation of an alcohol via halogenative decarboxylation. The method includes the step of reacting an alcohol of the formula R.sup.1 C(CX.sub.3).sub.2 OH with an alpha-haloester of the formula X.sup.2 CH.sub.2 CO.sub.2 R.sup.2 to form an alpha-alkoxy ester, wherein R.sup.1 is selected from the group consisting of hydrogen and alkyl groups, wherein R.sup.2 is selected from the group consisting of hydrogen and alkyl groups, wherein X, at each occurrence, is independently selected from the group consisting of hydrogen, bromine, fluorine, and chlorine, and wherein X.sup.2 is selected from the group consisting of bromine and chlorine. The resulting alpha-alkoxy ester is saponified to form an alpha-alkoxy acid which is heated at reflux with lead tetraacetate and a chlorinating agent to form a chloride compound of the formula R.sup.1 C(CX.sub.3).sub.2 OCH.sub.2 Cl. The chloride compound is converted to a fluoride compound of the formula R.sup.1 C(CX.sub.3).sub.2 OCH.sub.2 F with a fluorinating agent.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.