JP2790606B2 - Method for producing tetrakis (pentafluorophenyl) borate derivative using pentafluorophenyl alkali metal salt prepared from pentafluorobenzene - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel process for producing a tetrakis (pentafluorophenyl) borate derivative using pentafluorobenzene. The boron derivative obtained in the present invention is a very useful substance as an intermediate of a co-catalyst for polymerization of a cationic complex.

[0002]

2. Description of the Related Art In recent years,
The use of a tetrakis (pentafluorophenyl) borate derivative and a cyclopentadienyl transition metal complex, a so-called metallocene derivative, to generate a cation complex, and the scientific literature or patents on the study of the polymerization reaction using this as a catalyst has increased remarkably. For example, Macromol. Chem. Rapid Commu
n., 2 , pp. 663-667 (1991). However, in the production of tetrakis (pentafluorophenyl) borate derivatives, relatively expensive pentafluorobenzene bromide has been used as a starting material for a pentafluorophenyl group source.

According to the method, pentafluorobenzene bromide is subjected to a bromine-metal exchange reaction using an organometallic compound such as butyllithium to generate pentafluorophenyllithium, and boron trichloride or boron trifluoride is used as a starting material of a boron source. Or react directly with pentafluorobromobenzene with magnesium to generate Grignard reagents such as pentafluorophenylmagnesium bromide and react with boron trichloride or boron trifluoride as a starting material for the boron source Thus, tris (pentafluorophenyl) borane was synthesized, and then reacted with pentafluorophenyllithium to produce a tetrakis (pentafluorophenyl) borate derivative (J. Organometallic Che).
m., 2 , 245-250 (1964)).

[0004] Brominated pentafluorobenzene can be obtained by brominating pentafluorobenzene. However, if a tetrakis (pentafluorophenyl) borate derivative can be directly produced from pentafluorobenzene, the number of production steps can be reduced by one step. And the price of starting materials is reduced. A literature has already been published in which pentafluorophenyllithium or pentafluorophenylmagnesium bromide is generated and reacted using pentafluorobenzene as a starting material (J. Che.
m. Soc., 166 (1959), Synthesis of Fluoroorganic C
ompounds p.141, J. Org.Chem., 29, 2385 (1964) and
ibid, 31 , 4229 (1966)), and no application to the production of tetrakis (pentafluorophenyl) borate derivatives.

[0005]

Means for Solving the Problems In view of the above-mentioned situation, the present inventors have changed from a method in which pentafluorobenzene bromide was used as a starting material to the production of a tetrakis (pentafluorophenyl) borate derivative to pentafluorobenzene. The present invention has been achieved by variously examining a method of synthesizing a relatively expensive pentafluorobenzene bromide as a starting material by eliminating the step of brominating pentafluorobenzene by making a change.

That is, the gist of the present invention is that the formula [I]
For one equivalent of pentafluorobenzene represented by
By reacting 0.5 to 1.5 equivalents of the organometallic compound represented by the formula [II] in an ether solvent, a hydrocarbon solvent or a mixed solvent of an ether solvent and a hydrocarbon solvent at -120 to 80 ° C, A pentafluorophenyl alkali metal salt represented by the formula [III] is generated, and 3.7 equivalents or more of the formula [II
A method for producing a tetrakis (pentafluorophenyl) borate derivative represented by the formula [VII] by reacting a pentafluorophenyl metal compound represented by the formula [I] or 1 equivalent of pentafluorobenzene represented by the formula [I] By reacting 0.5 to 1.5 equivalents of an organometallic compound represented by the formula [II] in an ether solvent, a hydrocarbon solvent or a mixed solvent of an ether solvent and a hydrocarbon solvent at -120 to 80 ° C. To generate a pentafluorophenyl alkali metal salt represented by the formula [III], and to obtain 0.8 equivalent or more of the pentade represented by the formula [III] per 1 equivalent of the trispentafluorophenylborane represented by the formula [VIII]. The present invention relates to a method for producing a tetrakis (pentafluorophenyl) borate derivative represented by the formula [VIII] by reacting a fluorophenyl metal compound.

[0007]

The present invention will be specifically described below. The ether solvent referred to in the present invention is diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether,
Diisoamyl ether, 1,2-dimethoxyethane,
1,2-diethoxyethane, di-2-methoxyethyl ether, tetrahydrofuran, tetrahydropyran,
Shows 1,4-dioxane and the like.

[0008] Next, the hydrocarbon solvent referred to in the present invention includes pentane, isopentane, hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, n-paraffin or petroleum ether. Such as benzene, toluene, o-xylene, m-
Xylene, p-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,2,5-
Aromatic hydrocarbons such as trimethylbenzene, 1,3,5-trimethylbenzene, ethylbenzene, propylbenzene and butylbenzene, and mixtures thereof are shown.

Next, in the formula [II] of the present invention, the functional groups which do not affect the reaction include methyl group, ethyl group,
Propyl, isopropyl, propenyl, 2-isopropenyl, allyl, butyl, sec-butyl,
tert-butyl, isobutyl, pentyl, sec-pentyl, tert-pentyl, neo-pentyl, isopentyl, sec-isopentyl, hexyl, sec
-Hexyl group, isohexyl group, sec-isohexyl group, cyclohexyl group, phenyl group, benzyl group, o-
A tolyl group, an m-tolyl group, a p-tolyl group, a methoxymethyl group, a methylthiomethyl group, a 2-dimethylaminoethyl group, an o-anis group, a m-anis group, a p-anis group, a trimethylsilylmethyl group, Examples of the organometallic compound represented by the formula [II] include methyl lithium, ethyl lithium, propyl lithium, isopropyl lithium, butyl lithium, isobutyl lithium, sec-butyl lithium, tert-butyl lithium, pentyl lithium, isopentyl lithium, sec -Pentyl lithium, tert-pentyl lithium, sec-isopentyl lithium, hexyl lithium, isohexyl lithium, sec-hexyl lithium, cyclohexyl lithium, phenyl lithium, o
-Tolyl lithium, m-tolyl lithium, p-tolyl lithium, tolmethylsilyl lithium, phenyl sodium, o-tolyl sodium, m-tolyl sodium, p
-Tolyl sodium, butyl lithium / potassium tert-
Butoxide or butyl lithium / sodium tert-
Butoxide, etc., desirably, strongly basic, isopropyl lithium, sec-butyl lithium, tert-butyl lithium, sec-pentyl lithium, tert-pentyl lithium, sec-isopentyl lithium, sec-isopentyl lithium, sec-butyl lithium, sec-butyl lithium, which does not easily affect the reaction Hexyllithium or cyclohexyllithium.

Next, examples of the boron compound represented by the formula [V] in the present invention include boron trifluoride, boron trichloride, boron tribromide, boron triiodide, trimethyl boric acid, triethyl boric acid, Tripropyl boric acid, triisopropyl boric acid, tributyl boric acid, trimethylene borate, tris (dimethylamino) boron, tris (diethylamino) boron, tripyrrolidino boron, tripiperidino boron or trimorpholino boron. Further, complexes such as boron trifluoride diethyl ether complex, boron trifluoride dibutyl ether complex, boron trifluoride dimethyl sulfide complex, boron trichloride diethyl ether complex and boron trichloride dibutyl ether complex also fall into this category.

The specific method of manufacturing will be described below in order. The pentafluorobenzene represented by the formula [I] is dissolved in an ether solvent, a hydrocarbon solvent, or a mixed solvent thereof. 0.5 to 1.5 equivalents of the organometallic compound represented by the formula [II] is reacted with 1 equivalent of pentafluorobenzene in the range of -120 to 80 ° C.

In this reaction, when the pentafluorophenyl alkali metal salt represented by the formula [III] is generated, the pentafluorobenzene represented by the formula [I] is converted from the pentafluorobenzene represented by the formula [I]
When the amount of the organometallic compound represented by the formula is too small, a large amount of unreacted pentafluorobenzene remains, and when used in excess, the fluorine of the pentafluorophenyl metal salt represented by the formula [III] formed also undergoes halogen-metal exchange. It is preferable to use 0.8 to 1.20 equivalents of the organometallic compound represented by the formula [II] because of the possibility of reaction, and the reaction temperature is -80 ° C.
If the temperature is too low, the progress of the reaction is extremely slow. If the temperature is higher than 0 ° C., the progress of the side reaction is extremely fast, and in each case, the yield is extremely low. Therefore, it is desirable to carry out the reaction in the range of -80 to 0C. The reaction mixture is kept at the same temperature for 5 minutes.
By reacting for 120 minutes, an alkali metal salt of pentafluorophenyl represented by the formula [III] is prepared. .

The pentafluorophenyl alkali metal salt represented by the formula [III] produced here is C ₆ F ₅ Li, C
₆ F ₅ Na, a C ₆ F ₅ K.

When the boron compound represented by the formula [IV] is used in the reaction, the theoretical amount of the pentafluorophenyl alkali metal salt used is 4 equivalents, but is shown here.
If the amount is less than 3.7 equivalents, the yield of the tetrakis (pentafluorophenyl) borate derivative is remarkably reduced, so it is desirable to use 3.7 equivalents or more.

Further, tris (pentafluorophenyl)
When borane is used as a boron compound in the reaction, the theoretical amount is 1 equivalent, but if it is less than 0.7 equivalent shown here, the yield of the tetrakis (pentafluorophenyl) borate derivative is remarkably reduced, so that it is necessary to use 0.7 equivalent or more. desirable.

If the mixing temperature of the pentafluorophenyl alkali metal salt and the boron compound is lower than -100 ° C., the reaction proceeds extremely slowly. Therefore, a temperature higher than this is desirable. If it is higher than 0 ° C., the side reaction proceeds extremely. Temperatures below this are desirable because they are faster and in each case the yield is very low.

If the reaction temperature is lower than -100 ° C., the progress of the reaction is extremely slow. If the reaction temperature is higher than 0 ° C., unreacted pentafluorophenyl alkali metal salt is decomposed, so
It is desirable to carry out the reaction at a temperature of about 0.

[0018]

【The invention's effect】

According to the present invention, a tetrakis (pentafluorophenyl) borate derivative, which is an important intermediate of a cocatalyst in preparing a cationic complex polymerization catalyst, is prepared from less expensive pentafluorobenzene instead of pentafluorobenzene bromide. The effect of the present invention is enormous in that a method for producing a tetrakis (pentafluorophenyl) borate derivative at a high yield through a pentafluorophenyl alkali metal salt can be provided.

[0019]

The present invention will be described in more detail with reference to the following examples, which do not depart from the gist of the present invention, and are not limited by the following examples.

The reaction yield can be determined by quantifying the amount of a tetrakis (pentafluorophenyl) borate derivative produced using pentafluorotoluene as an internal standard substance by ¹⁹ F-NMR, or by using N, N-dimethylanilinium chloride or tributyl chloride. after induction by exchanging pair cation of N, N- dimethylanilinium or tributylammonium tetrakis (pentafluorophenyl) borate with ammonium, calculated based on the dry weight of the crystals, pentafluorotoluene as an internal standard ¹⁹
Purity was measured by F-NMR.

Example 1 A 50 ml glass dropping funnel, a temperature resistor and a septum rubber were attached to a 100 ml glass three-necked flask, and the inside of the system was sufficiently purged with nitrogen. 5 g (29.8 mmol) of pentafluorobenzene and 30 ml of diethyl ether are charged into the flask, and the solution is cooled to -65 ° C. Thereafter, a pentane solution (12.3 g, 29.8 mmol) of 16.1 wt% tert-butyl lithium charged in the dropping funnel was cooled to an internal temperature of-.
Add dropwise while not exceeding 55 ° C. After dropping
Stir at 65-55 ° C to prepare pentafluorophenyllithium. To the prepared solution of pentafluorophenyllithium was added a 1 mol / L boron trichloride hexane solution (7.45 mL, 7.45 mmol) at -65 to -55 ° C, and the mixture was stirred at the same temperature for 30 minutes, then heated to room temperature and reacted. Diethyl ether is removed from the mixture by distillation, and the organic layer is washed three times with 20 mL of water. After the aqueous layers are combined, when the aqueous layer is reacted with an aqueous solution of 1.1 equivalents of N, N-dimethylanilinium chloride with respect to the boron source, white crystals precipitate. The obtained crystals were filtered, washed with water, and dried under vacuum to obtain N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate at a yield of 92.3%. ^The purity was measured by ¹ H and ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance.
It was over 98wt%.

Example 2 Pentafluorobenzene (4.
40g, 26.2mmol) and diethyl ether (50ml)
20 wt% tert-butyllithium / pentane solution (7.98
g, 25.0 mmol) is added dropwise while maintaining the temperature of the reaction solution at -55 to -65 ° C, and after completion of the addition, the mixture is stirred for about 0.5 hour while maintaining the temperature of the reaction solution at -25 to -50 ° C. Thereafter, a 20.0 wt% tris (pentafluorophenyl) borane / toluene solution (63.8 g, 25.0 mmol) was mixed while maintaining the temperature of the reaction solution at −25 to −40 ° C., and the mixture was stirred at the same temperature for 30 minutes and then allowed to reach room temperature. Diethyl ether is removed by distillation from the solution of lithium tetrakis (pentafluorophenyl) borate obtained by raising the temperature, and the organic layer is washed three times with 20 mL of water. After the aqueous layers are combined, when the aqueous layer is reacted with an aqueous solution of 1.1 equivalents of N, N-dimethylanilinium chloride with respect to the boron source, white crystals precipitate. The obtained crystals were filtered, washed with water, and then dried under vacuum to obtain N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate at a yield of 97.3%. ^{When the} purity was measured by ¹ H and ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance, it was 98% by weight or more.

Example 3 Pentafluorobenzene (4.
40g, 26.2mmol) and diethyl ether (50ml)
20 wt% sec-butyllithium / hexane solution (7.98
g, 25.0 mmol) is added dropwise while maintaining the temperature of the reaction solution at -55 to -65 ° C, and after completion of the addition, the mixture is stirred for about 0.5 hour while maintaining the temperature of the reaction solution at -25 to -50 ° C. Thereafter, a 20.0 wt% tris (pentafluorophenyl) borane / toluene solution (63.8 g, 25.0 mmol) was mixed while maintaining the temperature of the reaction solution at −25 to −40 ° C., and the mixture was stirred at the same temperature for 30 minutes and then allowed to reach room temperature. Diethyl ether is removed by distillation from the solution of lithium tetrakis (pentafluorophenyl) borate obtained by raising the temperature, and the organic layer is washed three times with 20 mL of water. After the aqueous layers are combined, when the aqueous layer is reacted with an aqueous solution of 1.1 equivalents of N, N-dimethylanilinium chloride with respect to the boron source, white crystals precipitate. The obtained crystals were filtered, washed with water, and dried under vacuum to obtain N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate at a yield of 96.1%. ^The purity was measured by ¹ H and ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance.
That was all.

Example 4 A 100 ml glass three-necked flask was equipped with a 50 ml glass dropping funnel, a temperature resistor and a septum rubber, and the system was sufficiently purged with nitrogen. 5 g (29.8 mmol) of pentafluorobenzene and 30 ml of diethyl ether are charged into the flask, and the solution is cooled to -65 ° C. Thereafter, the internal temperature of the pentane solution (12.3 g, 29.8 mmol) of 16.1 wt% tert-butyllithium charged in the dropping funnel was-
Add dropwise while not exceeding 55 ° C. After dropping
Stir at 65-55 ° C to prepare pentafluorophenyllithium. To the prepared solution of pentafluorophenyllithium was added a 1 mol / L boron trichloride hexane solution (7.45 mL, 7.45 mmol) at -65 to -55 ° C, and the mixture was stirred at the same temperature for 30 minutes, and then heated to room temperature to be cooled. After filtering the generated lithium chloride, the yield of the obtained solution of lithium tetrakis (pentafluorophenyl) borate determined by ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance was 94.3%.

Example 5 Pentafluorobenzene (1
After cooling a solution of 5.8 g (100.0 mmol) and diethyl ether (100 ml) to −40 ° C., a 25 wt% tert-butyllithium / pentane solution (22.5 g, 88.0 mmol) was added, and the mixture was added at −30 to −40 ° C.
And stir for 22 hours. Then, 1.0 mol / L boron trichloride /
A hexane solution (21.0 ml, 21.0 mmol) is added at -40 ° C, and the temperature is raised to room temperature over 2 hours. Diethyl ether is removed by distillation from the obtained solution of lithium tetrakis (pentafluorophenyl) borate, and the organic layer is washed three times with 30 mL of water. After combining the aqueous layers, the aqueous layer
When an equivalent amount of an aqueous solution of tributylammonium chloride is reacted, white crystals precipitate. The resulting crystals are filtered, washed with water, and then dried under vacuum to obtain tributylammonium tetrakis (pentafluorophenyl) borate in a yield.
Obtained at 95.2%. ^The purity was measured by ¹ H and ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance and found to be 98% by weight or more.

Example 6 Pentafluorobenzene (1
After cooling a solution of 4.8 g (88.0 mmol) and diethyl ether (100 ml) to −40 ° C., a 20 wt% butyllithium / hexane solution (28.1 g, 87.7 mmol) was added, and the mixture was stirred at −30 to −40 ° C. for 10 hours. I do. Thereafter, boron trifluoride diethyl etherate (2.84 g, 20.0 mmol) is added at -40 ° C, and the temperature is raised to room temperature over 2 hours. After stirring overnight at room temperature, toluene (200 ml) was added, and then diethyl ether and hexane were distilled off by heating, and then toluene was further distilled off by heating to such an extent that about 30% of the charged amount was recovered. After filtering the precipitated lithium fluoride, the toluene was concentrated to dryness to obtain lithium tetrakis (pentafluorophenyl) borate in a yield of 51%.

Example 7 Pentafluorobenzene (1
After cooling a solution of 4.8 g (88.0 mmol) and diethyl ether (100 ml) to −40 ° C., a 24% by weight tert-butyllithium / pentane solution (23.4 g, 87.7 mmol) was added, and the mixture was added at −30 to −40 ° C.
And stir for 10 hours. Thereafter, boron trifluoride diethyl etherate (2.84 g, 20.0 mmol) is added at -40 ° C, and the temperature is raised to room temperature over 2 hours. After stirring overnight at room temperature, toluene (20
0 ml), and diethyl ether and hexane are distilled off by heating, and further, toluene is further distilled off by heating to the extent that about 30% of the added amount of toluene is recovered. After filtering the precipitated lithium fluoride, the toluene was concentrated to dryness to obtain lithium tetrakis (pentafluorophenyl) borate at a yield of 68%.

Example 8 Pentafluorobenzene (1
After cooling a solution of 5.1 g, 90.0 mmol) and diethyl ether (100 ml) to −40 ° C., a 20 wt% sec-butyllithium / hexane solution (28.2 g, 88.0 mmol) was added, and the temperature was changed from −30 to −40 ° C.
And stir for 10 hours. Thereafter, boron trifluoride diethyl etherate (2.84 g, 20.0 mmol) is added at -40 ° C, and the temperature is raised to room temperature over 2 hours. After stirring overnight at room temperature, toluene (20
0 ml), and diethyl ether and hexane are distilled off by heating, and further, toluene is further distilled off by heating to the extent that about 30% of the added amount of toluene is recovered. After filtering the precipitated lithium fluoride, the toluene was concentrated to dryness to obtain lithium tetrakis (pentafluorophenyl) borate at a yield of 65%.

Example 9 Pentafluorobenzene (1
After cooling a solution of 4.8 g (88.0 mmol) and diethyl ether (100 ml) to −40 ° C., a 15 wt% butyl sodium / hexane solution (47.0 g, 88.0 mmol) was added, and the mixture was heated at −30 to −40 ° C.
Stir for hours. Thereafter, boron trifluoride diethyl etherate (2.84 g, 20.0 mmol) is added at -40 ° C, and the temperature is raised to room temperature over 2 hours. Diethyl ether is removed by distillation from the obtained solution of sodium tetrakis (pentafluorophenyl) borate, and the organic layer is washed three times with 20 mL of water. After the aqueous layers are combined, when the aqueous layer is reacted with an aqueous solution of 1.1 equivalents of N, N-dimethylanilinium chloride with respect to the boron source, white crystals precipitate. The obtained crystals were filtered, washed with water, and dried under vacuum to obtain N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate at a yield of 86.1%. ^The purity was measured by ¹ H and ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance and found to be 98% by weight or more.

Example 10 Pentafluorobenzene (1
After cooling a solution of 6.8 g (100.0 mmol) and dibutyl ether (100 ml) to −40 ° C., a 20 wt% sec-butyllithium / hexane solution (28.2 g, 88.0 mmol) was added, and the temperature was changed from −30 to −40 ° C.
And stir for 2 hours. Thereafter, boron trifluoride diethyl etherate (2.84 g, 20.0 mmol) is added at -40 ° C, and the temperature is raised to room temperature over 2 hours. After stirring overnight at room temperature, octane (200
ml), and diethyl ether and hexane are distilled off by heating. Then, octane is further distilled off by heating so that about 30% of the added amount is recovered. After filtering the precipitated lithium fluoride, the octane was concentrated to dryness to obtain lithium tetrakis (pentafluorophenyl) borate at a yield of 67.3%.

Example 11 Pentafluorobenzene (1
4.8 g, 88.0 mmol) and diisopropyl ether (100 ml)
After cooling the solution to −40 ° C., an 18 wt% sec-butyllithium / hexane solution (31.3 g, 88.0 mmol) was added, and the solution was added at −30 ° C.
And stirred at −40 ° C. for 0.5 hour. Then, add 1 mol / L boron trichloride / hexane solution (20 mL, 20.0 mmol) at -40 ° C.
And raise the temperature to room temperature over 2 hours. Diisopropyl ether is removed by distillation from the obtained solution of lithium tetrakis (pentafluorophenyl) borate to remove the organic layer.
Wash three times with 20 mL of water. After the aqueous layers are combined, when the aqueous layer is reacted with an aqueous solution of 1.1 equivalents of N, N-dimethylanilinium chloride with respect to the boron source, white crystals precipitate. The obtained crystals were filtered, washed with water, and dried under vacuum to obtain N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate in a yield of 95.1%. ¹ H and
^The purity was measured by ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance and found to be 98 wt% or more.

Example 12 Pentafluorobenzene (1
After cooling a solution of 4.8 g (88.0 mmol) and diethyl ether (100 ml) to −40 ° C., a 15 wt% tert-butyllithium / pentane solution is added, and the mixture is stirred at −30 to −40 ° C. for 30 hours. Then, trimethyl boric acid (2.08 g, 20.0 mmol) was added at -40 ° C.
And raise the temperature to room temperature over 2 hours. After stirring overnight at room temperature, octane (200 ml) was added, and diethyl ether was removed by distillation. The organic layer was washed three times with 20 mL of water. After combining the aqueous layers, 1.1 equivalents of N, N-
When an aqueous solution of dimethylanilinium is reacted, white crystals precipitate. The obtained crystals were filtered, washed with water, and then dried under vacuum to obtain N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate at a yield of 83.2%.
I got it. ^The purity was measured by ¹ H and ¹⁹ F-NMR using pentafluorotoluene as an internal standard substance.
wt% or more.

──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Kenji Ishimaru 1-1-1, Miyamae, Shinnanyo-shi, Yamaguchi Prefecture Isshin Ryo (56) References JP-A-63-238087 (JP, A) JP-A-39-26394 (JP, B1) (58) Fields investigated (Int. Cl. ⁶ , DB name) C07F 5/02 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. An equivalent of pentafluorobenzene represented by the following formula [I] C ₆ HF ₅ [I]:
0.5 to 1.5 equivalents of the general formula [II] RM [II] (wherein M represents an alkali metal ion, R represents a hydrocarbon group having 1 to 10 carbon atoms, and the hydrocarbon group has an effect on the reaction. The organic metal compound represented by the formula (1) may be reacted in an ether solvent, a hydrocarbon solvent or a mixed solvent of an ether solvent and a hydrocarbon solvent at -120 to 80 ° C. By the following general formula [I
II] C ₆ F ₅ M [III] (wherein M represents an alkali metal ion) to generate a pentafluorophenyl alkali metal salt represented by the following general formula [IV] BX ₃ [IV] [ In the formula, X is a halogen or the following general formula [V] OR [V] (wherein, R represents a hydrocarbon group having 1 to 10 carbon atoms, and the hydrocarbon group has a functional group that does not affect the reaction. Or a substituent represented by the following general formula [VI] NRR '[VI] (wherein R and R' are the same or different hydrogen or carbon atoms having 1 to 1 carbon atoms) 20 hydrocarbon groups, and the hydrocarbon groups may contain a functional group that does not affect the reaction, and R and R ′ may be bonded to each other to form a ring.) And may form a one-to-one complex with an ether-based solvent. The boron compound represented by the formula [III] is reacted with 3.7 equivalents or more of a pentafluorophenyl metal compound represented by the formula [III] per 1 equivalent of the boron compound represented by the following general formula [VII] (C ₆ F ₅ ) ₄ BM [VII (Wherein M represents an alkali metal ion.) A method for producing a tetrakis (pentafluorophenyl) borate derivative represented by the following formula: 2. A compound of the formula [II]
I] to generate a pentafluorophenyl alkali metal salt, and at least 0.8 equivalent to 1 equivalent of trispentafluorophenylborane represented by the following formula [VIII] (C ₆ F ₅ ) ₃ B [VIII] A method for producing a tetrakis (pentafluorophenyl) borate derivative represented by the formula [VII] (C ₆ F ₅ ) ₄ BM [VII] by reacting a pentafluorophenyl metal compound represented by the formula [III].