Fluoroalkylating agent
AssigneeKumiai Chemical Industry Co., Ltd.
InventorsKentaro Kawazoe, Kotaro Yoshioka
Life of this patent
Estimating the term…
Abstract
Problem to be Solved It is intended to provide an industrially preferable fluoroalkylating agent and use thereof. Solution The present invention provides a fluoroalkylating agent represented by the general formula (1) wherein R1 is a C1 to C8 fluoroalkyl group; R2 and R3 are each independently a C1 to C12 alkyl group or the like; Y1 to Y4 are each independently a hydrogen atom, a halogen atom, or the like; and X− is a monovalent anion. A compound of the general formula (3): R4—S—R1 having an introduced C1 to C8 fluoroalkyl group is easily obtained by reacting a compound of the general formula (2): R4—S—Z wherein R4 is a hydrocarbon group or the like; and Z is a leaving group, with the compound of the general formula (1).
Claims6
A method for the production of a target compound having R1, wherein R1 is as defined below, which comprises reacting a starting compound with a fluoroalkylating agent represented by the general formula (1):
- wherein R1 is a C1 to C8 fluoroalkyl group;
- R2 and R3 are each independently
- a C1 to C12 alkyl group which may have one or more substituents,
- a C2 to C6 alkenyl group which may have one or more substituents,
- a C2 to C6 alkynyl group which may have one or more substituents,
- a C3 to C8 cycloalkyl group which may have one or more substituents, or
- a C6 to C10 aryl group which may have one or more substituents;
- Y1, Y2, Y3 and Y4 are each independently
- a hydrogen atom, a halogen atom, a nitro group, a cyano group,
- a C1 to C12 alkyl group which may have one or more substituents,
- a C2 to C6 alkenyl group which may have one or more substituents,
- a C2 to C6 alkynyl group which may have one or more substituents,
- a C3 to C8 cycloalkyl group which may have one or more substituents,
- a hydroxy group,
- a C1 to C6 alkoxy group,
- a C1 to C6 alkylthio group, a C1 to C6 alkylsulfinyl group, a C1 to C6 alkylsulfonyl group,
- an amino group, a mono (C1 to C6 alkyl) amino group, a di (C1 to C6 alkyl) amino group,
- a C1 to C6 acylamino group,
- a formyl group, a C2 to C6 acyl group,
- a C1 to C6 alkoxycarbonyl group,
- a C6 to C10 aryl group which may have one or more substituents, or
- a heterocyclic group which may have one or more substituents, wherein the said heterocyclic group is a 5- to 10-membered heterocyclic group having 1 to 9 carbon atoms and 1 to 4 heteroatoms selected independently from a nitrogen atom, an oxygen atom and a sulfur atom, or two adjacent substituents of Y1 and Y2, Y2 and Y3, or Y3 and Y4, together with carbon atoms to which these substituents are attached, form a 4- to 8-membered carbocyclic ring or a 4- to 8-membered heterocyclic ring having 1 to 4 heteroatoms selected independently from an oxygen atom, a sulfur atom and a nitrogen atom, wherein the said formed ring may have one or more substituents;
- and
- X− is a monovalent anion,
- wherein
- a) the target compound is a compound represented by the general formula (3):
- the starting compound is a compound represented by the general formula (2):
- wherein R1 is a C1 to C4 perfluoroalkyl group,
- R4 is a straight chain or branched chain hydrocarbon group which may have one or more substituents,
- a cyclic hydrocarbon group which may have one or more substituents, or
- a heterocyclic group which may have one or more substituents,
- Z is a leaving group;
- or
- b) the target compound is a compound represented by the general formula (5):
- the starting compound is a compound represented by the general formula (4):
- wherein R1 is a C1 to C4 perfluoroalkyl group,
- R5 is
- a straight chain or branched chain hydrocarbon group which may have one or more substituents,
- a cyclic hydrocarbon group which may have one or more substituents, or
- a heterocyclic group which may have one or more substituents;
- and
- R6 is
- a hydrogen atom,
- a straight chain or branched chain hydrocarbon group which may have one or more substituents,
- a cyclic hydrocarbon group which may have one or more substituents, or
- a heterocyclic group which may have one or more substituents;
- wherein, the one or more substituents in each case is independently selected from the group consisting of a halogen atom, a nitro group, a cyano group,
- a C1 to C6 alkyl group,
- a C2 to C6 alkenyl group,
- a C2 to C6 alkynyl group,
- a C3 to C8 cycloalkyl group,
- a C1 to C6 haloalkyl group,
- a hydroxy group,
- a C1 to C6 alkoxy group,
- a C1 to C6 haloalkoxy group,
- a C1 to C6 alkylthio group, a C1 to C6 alkylsulfinyl group, a C1 to C6 alkylsulfonyl group,
- a C1 to C6 haloalkylthio group, a C1 to C6 haloalkylsulfinyl group, a C1 to C6 haloalkylsulfonyl group,
- an amino group, a mono (C1 to C6 alkyl) amino group, a di (C1 to C6 alkyl) amino group,
- a C1 to C6 acylamino group,
- a formyl group, a C2 to C6 acyl group,
- a C1 to C6 alkoxycarbonyl group,
- a mono (C1 to C6 alkyl) aminocarbonyl group, a di (C1 to C6 alkyl) aminocarbonyl group,
- a C6 to C10 aryl group,
- a C6 to C10 aryloxy group,
- a C6 to C10 aryl C1 to C4 alkyl group, and
- a heterocyclic group, wherein the heterocyclic group is a 5- to 10-membered heterocyclic group having 1 to 9 carbon atoms and 1 to 4 heteroatoms selected independently from a nitrogen atom,
- an oxygen atom and a sulfur atom,
- in the presence of a base.
Dependencies are inferred from the claim text.