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Compound manufacturing method

A manufacturing method and compound technology, which is applied in the preparation of organic compounds, hydrocarbons, hydrocarbons, etc., can solve the problems of undocumented organic base manufacturing methods, and achieve the effect of excellent and high reaction speed

Active Publication Date: 2020-12-22
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be noted that Patent Document 3 does not describe a method for producing a compound using an organic base

Method used

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  • Compound manufacturing method
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0531] Hereinafter, although an Example demonstrates this invention in detail, this invention is not limited to these Examples.

[0532]

[0533] Measuring device: CBM-20A (manufactured by Shimadzu Corporation)

[0534] Column: L-Column2 ODS (3μm, 4.6mmφ×25cm)

[0535] Mobile Phase A: Acetonitrile

[0536] Mobile phase B: THF

[0537] Mobile phase C: pure water

[0538] Gradient: 0.01 minutes A=60%, B=0%, C=40%

[0539] 10 minutes A=60%, B=0%, C=40%

[0540] 20 minutes A=100%, B=0%, C=0%

[0541] 100 minutes A=100%, B=0%, C=0%

[0542] 120 minutes A=0%, B=100%, C=0%

[0543] 130 minutes A=0%, B=100%, C=0%

[0544] Flow: 1.0mL / min

[0545] Detection wavelength: 280nm.

[0546]

[0547] Measuring device: HLC-822GPC (manufactured by Tosoh Corporation)

[0548] Column: PLgel 10 μm MIXED-B (manufactured by Tosoh Corporation)

[0549] Column temperature: 40°C

[0550] Mobile phase: tetrahydrofuran

[0551] Flow rate: 1.5mL / min

[0552] Detection wavelength: 228nm....

Embodiment 1

[0571] Synthesis of compound (5-1)

[0572] Compound (1-1) was synthesized according to the method described in International Publication No. 2002 / 045184.

[0573] For the compound (2-1), 4-biphenylboronic acid manufactured by Tokyo Chemical Industry Co., Ltd. was used.

[0574] After the reaction vessel was made into a nitrogen gas atmosphere, compound (1-1) (1.93g), compound (2-1) (2.43g), phenanthrene (0.316g) (internal standard substance), dichlorobis[tris (2-Methoxyphenyl)phosphine]palladium (1.18mg), toluene (100g) and pinacol (0.26g), heated to 86°C. Then, 20% tetraethylammonium hydroxide aqueous solution (15g) was added there, and it stirred at 86 degreeC for 2 hours. As a result of LC analysis of the obtained reaction mixture, the internal standard yield of the target compound (5-1) was 99%. The results are shown in Table 1.

[0575] [Table 1]

[0576] .

[0577] From the comparison of the yield of compound (5-1) in Comparative Example 1 and the yield of comp...

Synthetic example 1

[0578] Synthesis of Polymer Organic Compound P-1

[0579] [chemical formula 81]

[0580]

[0581] (In the formula, n represents the degree of polymerization).

[0582] Compound (1-2) was synthesized according to the method described in International Publication No. 2002 / 045184.

[0583] Compound (2-2) was synthesized according to the method described in US Patent No. 6,169,163.

[0584] After making the reaction vessel into a nitrogen gas atmosphere, compound (1-2) (7.22 g), compound (2-2) (9.90 g), dichlorobis[tris(2-methoxyphenyl)phosphine] were added Palladium (4.15 mg) and toluene (131 g), heated to 86°C. Then, 10% tetramethylammonium hydroxide aqueous solution (108g) and tetrabutylammonium bromide (0.51g) were added there, and it stirred at 86 degreeC for 2 hours. After cooling the obtained reaction mixture to room temperature, toluene (1096g) was added and diluted and liquid-separated, and water (324g) was added and liquid-separated. After dripping the obtained ...

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Abstract

Provided is a method for producing a compound having an excellent reaction rate (high reaction rate). A method for producing a compound, comprising: supplying a compound (1) having at least one atom selected from Group A, a compound (2) having at least one group selected from Group B, and a transition metal into a reaction vessel. The steps of catalyst, organic base, and compound having more than 2 hydroxyl groups; and, in the reaction vessel, compound (1) and compound ( 2) The steps of the reaction. <a组>Chlorine atom, bromine atom, iodine atom, etc. <b组>-B(R C2 ) 2 The group shown, ‑B(OR C2 ) 2 The groups shown, etc. (where, R C2 Indicates a hydrogen atom, an alkyl group, etc. There are multiple R C2 may be the same or different, and may be bonded to each other and form a ring together with the boron atom or oxygen atom to which each is bonded).

Description

technical field [0001] The present invention relates to methods for producing compounds. Background technique [0002] The production method of a compound using a coupling reaction of an organoboron compound and an organohalogen compound is a highly versatile production method. Therefore, organic semiconductor materials (such as organic electroluminescent materials, organic transistor materials, and organic solar cell materials), medical materials, agricultural chemical materials, liquid crystal materials, and the like are manufactured using this coupling reaction. [0003] Patent Documents 1 and 2 describe methods for producing compounds comprising the step of subjecting an organoboron compound and an organohalogen compound to a coupling reaction in the presence of a transition metal catalyst, an organic base, and an organic solvent. In addition, Patent Documents 1 and 2 do not describe a method for producing a compound using a compound having two or more hydroxyl groups. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/04C07C1/32C07C13/567C07C41/30C07C43/205C07C209/68C07C211/54C08G61/12C07B61/00
CPCC07C41/30C07B37/04C07C209/68C08G61/12C07C1/321C07C2523/44C07C2531/24C07C2603/18C08G2261/124C08G2261/148C08G2261/3142C08G2261/3162C08G2261/374C08G2261/411C07C13/567C07C43/205C07C211/56
Inventor 横井优季鹿岛健
Owner SUMITOMO CHEM CO LTD