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US 2014/0235898 A1Published application
Substituted Phenylsulfur Trifluoride and Other Like Fluorinating Agents
AssigneeUbe Industries, Ltd.
InventorTeruo UMEMOTO
Life of this patent
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Abstract
Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds. Finally, various intermediate compounds for use in preparing substituted phenylsulfur trifluorides are provided.
Claims13
A method of introducing one or more fluorine atoms into a target compound comprising:
- contacting a fluorinating agent of formula (I):
- in which
- R1a and R1b are independently a hydrogen atom;
- a primary or secondary alkyl group having from one to eight carbon atoms;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- and
- R2a and R2b are independently a hydrogen atom;
- a halogen atom;
- a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- R3 is a hydrogen atom;
- a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- and
- wherein, when R3 is a hydrogen atom, at least two of R1a, R1b, R2a, and R2b each is independently a halogen atom;
- a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms wherein R1a and R1b are not a halogen atom or a tertiary alkyl group;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- or, at least one of R1a, R1b, R2a, and R2b is a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- and
- wherein, when R3 is a primary alkyl group having one to eight carbon atoms, at least one of R1a, R1b, R2a, and R2b is a halogen atom;
- a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms wherein R1a and R1b are not a halogen atom or a tertiary alkyl group;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- and
- wherein, when at least two of R2a, R2b, and R3 are tertiary alkyl groups, the tertiary alkyl groups are non-adjacent;
- with the target compound under conditions that allow one or more fluorine atoms to be introduced into the target compound.
22 more elements
A method of introducing one or more fluorine atoms into a target compound comprising:
- contacting a fluorinating agent of formula (Ia):
- in which:
- R1a and R1b are independently a hydrogen atom;
- a primary or secondary alkyl group having from one to eight carbon atoms;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- R2a′ and R2b′ are independently a hydrogen atom or a halogen atom;
- and
- R3 is a hydrogen atom;
- a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms;
- or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- wherein when R3 is a hydrogen atom, R1a and R1b are independently a primary or secondary alkyl group having from one to eight carbon atoms or at least one of R1a and R1b is a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage, and
- wherein, when R3 is a primary alkyl group having one to eight carbon atoms, at least one of R1a and R1b is a primary or secondary alkyl group having from one to eight carbon atoms or a primary, secondary, or tertiary alkyl group having two to eight carbon atoms and at least one ether linkage;
- with the target compound under conditions that allow one or more fluorine atoms to be introduced into the target compound.
10 more elements
A method of introducing one or more fluorine atoms into a target compound comprising:
- contacting a fluorinating agent of formula (II):
- in which:
- R1a′ and R1b′ are independently a hydrogen atom or a primary or secondary alkyl group having from one to eight carbon atoms;
- and
- R3′ is a hydrogen atom, or a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms;
- wherein when R3′ is a hydrogen atom, R1a′ and R1b′ are independently a primary or secondary alkyl group having from one to eight carbon atoms, and wherein, when R3′ is a primary alkyl group having one to eight carbon atoms, at least one of R1a′ and R1b′ is a primary or secondary alkyl group having from one to eight carbon atoms;
- with the target compound under conditions that allow one or more fluorine atoms to be introduced into the target compound.
4 more elements
A method of introducing one or more fluorine atoms into a target compound comprising:
- contacting a fluorinating agent of formula (Ib):
- in which
- R3′ is a hydrogen atom, or a primary, secondary, or tertiary alkyl group having from one to eight carbon atoms;
- and
- R4 is a primary, secondary, or tertiary alkyl group;
- and
- R5 and R6 are independently an alkylene group;
- the number of total carbon atoms of R4, R5, and R6 is eight or less, and m is 0 or 1;
- with the target compound under conditions that allow one or more fluorine atoms to be introduced into the target compound.
6 more elements
Dependencies are inferred from the claim text.