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US 6,229,055 B1Granted
Synthesis of fluorinated xanthene derivatives
AssigneeMolecular Probes, Inc.
InventorsDieter H. Klaubert, Kyle R. Gee
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Abstract
Facile syntheses for fluorinated resorcinol and aminophenol derivatives are provided that yield isomer-free products in good yield. These novel methods use generally available precursors and standard laboratory reagents and equipment to reproducibly produce these synthetically useful reagents in relatively large quantities. The resulting fluorinated resorcinols and aniinophenols possess utility in the preparation of fluorinated fluorescein and rhodol dyes.
Claims16
A method of preparing a fluorinated resorcinol having the formula:
- wherein
- R1, R2 and R4 are independently hydrogen, fluorine, chlorine, hydroxy, alkyl having 1-6 carbons or alkoxy having 1-6 carbons;
- provided at least one of R1, R2 and R4 is fluorine;
- comprising the steps of:
- a) treating a substituted nitrofluorobenzene having the formula
- wherein
- R1 and R2 are independently hydrogen, fluorine, chlorine, alkyl having 1-6 carbons or alkoxy having 1-6 carbons;
- R4 is hydrogen, fluorine, chlorine, alkyl having 1-6 carbons, alkoxy having 1-6 carbons or nitro;
- R3 and R5 are independently alkoxy having 1-6 carbons, a benzyloxy or F;
- and
- R6 is H or nitro;
- provided that
- exactly one of R4 and R6 is nitro;
- at least one of R3 and R5 is F;
- and
- at least one of R1, R2 and R4 is F;
- with a displacing ion that is an alkoxide ion having 1-6 carbons or a benzyloxide ion to yield a nitroresorcinol diether,
- b) reducing the said nitroresorcinol diether to yield an aminoresorcinol diether;
- c) diazotizing said aminoresorcinol diether to yield a resorcinol diether diazonium salt;
- d) dediazotizing said resorcinol diether diazonium salt to yield a resorcinol diether;
- and
- e) cleaving said resorcinol diether to yield said fluorinated resorcinol.
19 more elements
Dependencies are inferred from the claim text.