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US 2022/0169667 A1Published application
Production method of biarylphosphine
AssigneeNippon Chemical Industrial Co., Ltd.
InventorsKen Tamura, Yuki Sawatsugawa, Natsuhiro Sano
Life of this patent
Estimating the term…
Abstract
A production method by which a biarylphosphine useful as a Buchwald phosphine ligand can be obtained in high purity is provided through an industrially advantageous process. The production method of a biarylphosphine comprises a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative with a benzene derivative to obtain a biphenyl derivative, and a step B of the reacting the biphenyl derivative with a halogenated phosphine. In the step A, the charge molar ratio of the halogenated benzene derivative to the benzene derivative is preferably 1.0 to 5.0.
Claims9
A production method of a biarylphosphine comprising:
- a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative represented by the following formula (1):
- wherein R1 to R3 represent an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a heteroaralkyl group, an alkoxy group or an amino group, and the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl group, the heteroaralkyl group, the alkoxy group and the amino group may be substituted with an alkyl group, a cycloalkyl group, a halogen group or an alkoxy group;
- R1 to R3 may be a same group or a different group;
- and X1 represents a halogen atom;
- with a benzene derivative represented by the following general formula (2):
- wherein R4 to R5 represent an alkyl group, an alkoxy group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a heteroaralkyl group or an amino group;
- and the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl groups, the heteroaralkyl group, the alkoxy groups and the amino group may be substituted with an alkyl group, a cycloalkyl group, a halogen groups or an alkoxy groups;
- R4 to R5 may be a same group or a different group;
- and X2 represents a halogen atom;
- to obtain a biphenyl derivative represented by a following general formula (3):
- wherein R1 to R5 are the same as described above;
- and a subsequent step B of reacting the biphenyl derivative with a halogenated phosphine represented by a following general formula (4):
- (R6)(R7)PX3 (4)
- wherein R6 to R7 represent an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group or a heteroaralkyl group;
- and R6 to R7 may be a same group or a different group;
- the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl group, and the heteroaralkyl group may be substituted with an alkyl group, a cycloalkyl group, a halogen group or an alkoxy group;
- and X3 represents a halogen atom;
- the biarylphosphine being represented by a following formula (5):
- wherein R1 to R7 are the same as described above.
16 more elements
A production method of a biarylphosphine comprising:
- a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative represented by the following formula (1):
- wherein R1 to R3 represent an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a heteroaralkyl group, an alkoxy group or an amino group, and the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl group, the heteroaralkyl group, the alkoxy group and the amino group may be substituted with an alkyl group, a cycloalkyl group, a halogen group or an alkoxy group;
- R1 to R3 may be a same group or a different group;
- and X1 represents a halogen atom;
- with a benzene derivative re resented by the following general formula (2):
- wherein R4 to R5 represent an alkyl group, an alkoxy group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a heteroaralkyl group or an amino group;
- and the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl groups, the heteroaralkyl group, the alkoxy groups and the amino group may be substituted with an alkyl group, a cycloalkyl group, a halogen groups or an alkoxy groups;
- R4 to R5 may be a same group or a different group;
- and X2 represents a halogen atom;
- to obtain a biphenyl derivative represented by a following general formula (3):
- wherein R1 to R5 are the same as described above;
- a subsequent step C of reacting the biphenyl derivative with a brominating agent or an iodinating agent to obtain a halogenated biphenyl derivative represented by the following general formula 6):
- wherein R1 to R5 are the same as described above, and A represents a bromine atom or an iodine atom;
- and a subsequent step D of reacting a lithiated product obtained through lithiation of the halogenated biphenyl derivative with a halogenated phosphine represented by a following general formula (4):
- (R6)(R7)PX3 (4)
- wherein R6 to R7 represent an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group or a heteroaralkyl group;
- and R6 to R7 may be a same group or a different group;
- the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl group, and the heteroaralkyl group may be substituted with an alkyl group, a cycloalkyl group, a halogen group or an alkoxy group;
- and X3 represents a halogen atom;
- the biarylphosphine being represented by a following formula (5):
- wherein R1 to R7 are the same as described above.
18 more elements
A production method of a halogenated biphenyl derivative comprising:
- a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative represented by the following formula (1):
- wherein R1 to R3 represent an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a heteroaralkyl group, an alkoxy group or an amino group, and the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl group, the heteroaralkyl group, the alkoxy group and the amino group may be substituted with an alkyl group, a cycloalkyl group, a halogen group or an alkoxy group;
- R1 to R3 may be a same group or a different group;
- and X1 represents a halogen atom;
- with a benzene derivative represented by the following general formula (2):
- wherein R4 to R5 represent an alkyl group, an alkoxy group, a cycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a heteroaralkyl group or an amino group;
- and the alkyl group, the cycloalkyl group, the aryl group, the heteroaryl group, the aralkyl groups, the heteroaralkyl group, the alkoxy groups and the amino group may be substituted with an alkyl group, a cycloalkyl group, a halogen groups or an alkoxy groups;
- R4 to R5 may be a same group or a different group;
- and X2 represents a halogen atom;
- to obtain a biphenyl derivative represented by a following general formula (3):
- wherein R1 to R5 are the same as described above;
- and a subsequent step D of reacting the biphenyl derivative with a brominating agent or an iodinating agent;
- the halogenated biphenyl derivative being represented by a following formula (6):
- wherein R1 to R5 are the same as described above, and A represents a bromine atom or an iodine atom.
11 more elements
Dependencies are inferred from the claim text.