KR20240069893A - Novel method for preparing high purity 9-phenylcarbazole - Google Patents
Novel method for preparing high purity 9-phenylcarbazole Download PDFInfo
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- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 8
- -1 halobenzene compound Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- 150000005171 halobenzenes Chemical class 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical group [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
본 발명은 올레드 소재로 유용한 삼성 시피엘의 합성용 중간체로써 고순도 9-페닐카바졸의 신규한 제조 방법에 관한 것으로, 본 발명의 제조방법은 강염기를 사용하여, 벤진 중간 단계를 이용한 반응공정이 단순하고 반응 컨트롤이 용이하며, 반응시간이 짧아 매우 효율적인 방법이며, 이로 인해 올레드 소재로 유용한 삼성 시피엘의 합성용 중간체로써 9-페닐카바졸의 순도를 높이는 효과가 있다.The present invention relates to a novel production method of high-purity 9-phenylcarbazole as an intermediate for the synthesis of Samsung CPL, which is useful as an OLED material. The production method of the present invention involves a reaction process using a strong base and a benzine intermediate step. It is simple, easy to control, and has a short reaction time, making it a very efficient method. This has the effect of increasing the purity of 9-phenylcarbazole as a synthetic intermediate for Samsung CPL, which is useful as an OLED material.
Description
본 발명은 올레드 소재로 유용한 시피엘의 합성용 중간체로써 고순도 9-페닐카바졸의 신규한 제조 방법에 관한 것이다.The present invention relates to a novel method for producing high purity 9-phenylcarbazole as an intermediate for the synthesis of CPI, which is useful as an OLED material.
올레드 소재로 삼성 시피엘을 고효율로 공업적으로 제조할 때의 중요 중간체로서, 9-페닐카바졸 유도체는 이미 공지되어 있다.9-phenylcarbazole derivatives are already known as important intermediates in the highly efficient industrial production of Samsung CPL from OLED materials.
이의 제조 방법으로서는, 특허 US20070282111 A1, WO2004072088 A2 또는 'Tetrahedron Letters (2000), 41(4), 481-483.'에서 원료인 9H-카바졸 화합물에 할로벤젠을 팔라듐 촉매 하에서 아민화 반응을 수행하여 9-페닐카바졸 유도체를 합성하는 방법이 알려져 있다. 그러나, 팔라듐 촉매를 사용하여 고순도의 9-페닐카바졸 유도체를 얻을 수 있으나 일반적으로 팔라듐 촉매는 고가의 원료로 상기 방법은 합성 단가가 높은 한계점이 있다.As a method for producing this, in patents US20070282111 A1, WO2004072088 A2 or 'Tetrahedron Letters (2000), 41(4), 481-483.', halobenzene is aminated to the raw material 9H-carbazole compound under a palladium catalyst. Methods for synthesizing 9-phenylcarbazole derivatives are known. However, high purity 9-phenylcarbazole derivatives can be obtained using a palladium catalyst, but the palladium catalyst is generally an expensive raw material, and this method has a limitation in that the synthesis cost is high.
본 발명의 목적은 9-페닐카바졸 유도체 유도체 화합물의 제조에 있어서 강염기를 사용하여 할로벤젠으로부터 벤진 중간체를 거쳐 수행되는 반응공정이 단순하고 반응시간이 짧아 경제성이 있으면서 안정성이 우수하고 높은 수율을 가지는 9-페닐카바졸 유도체 유도체의 신규한 제조방법을 제공하는 것이다.The purpose of the present invention is to produce a 9-phenylcarbazole derivative compound, in which the reaction process performed from halobenzene through a benzene intermediate using a strong base is simple and the reaction time is short, so it is economical, has excellent stability, and has high yield. To provide a new method for producing 9-phenylcarbazole derivatives.
본 발명은 하기 화학식 3의 화합물을 강염기와 반응시킨 후 화학식 2와 반응시켜 하기 화학식 1를 제조하는 단계를 포함하는 하기 화학식 1의 9-페닐카바졸 유도체 유도체의 신규한 제조 방법을 제공한다.The present invention provides a novel method for producing a 9-phenylcarbazole derivative of the following formula (1), which includes the step of reacting the compound of the formula (3) with a strong base and then reacting with the formula (2) to prepare the formula (1).
[화학식 1][Formula 1]
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[상기 화학식 1 내지 4에서,[In Formulas 1 to 4,
X은 Br 또는 Cl이며;X is Br or Cl;
M은 Li, Na 또는 K이다.]M is Li, Na or K.]
구체적으로 본 발명의 일 실시예에 따른 상기 화학식 1로 표시되는 9-페닐카바졸 유도체의 신규한 제조방법을 반응식으로 나타내면 하기 반응식 1로 나타낼수 이다.Specifically, the novel production method of the 9-phenylcarbazole derivative represented by Chemical Formula 1 according to an embodiment of the present invention can be expressed as Scheme 1 below.
[반응식 1][Scheme 1]
[반응식 1에서, M 및 X는 상기 화학식에서의 M 및 X의 정의와 동일하다.][In Scheme 1, M and X are the same as the definitions of M and X in the above formula.]
상세하게는 본 발명의 일 실시예에 따른 상기 화학식 1로 표시되는 9-페닐카바졸의 신규한 제조 방법은 상기 화학식 2의 화합물 할로벤젠을 강염기와 반응시켜 벤진 화합물을 중간체로 제조하여 상기 화학식 3의 화합물 9H-카바졸과 반응시켜 하기 화학식 1의 화합물 9-페닐카바졸을 제조하는 단계를 포함한다.In detail, the novel method for producing 9-phenylcarbazole represented by Formula 1 according to an embodiment of the present invention is to prepare a benzine compound as an intermediate by reacting the halobenzene compound of Formula 2 with a strong base to obtain Formula 3 It includes the step of reacting with compound 9 H -carbazole to prepare compound 9-phenylcarbazole of the formula 1 below.
본 발명은 9-페닐카바졸의 제조, 특히 상기 화학식 2의 화합물을 상기 화학식 1의 화합물로 제조하는데 있어서 고가의 팔라듐 촉매를 사용하지 않고 벤진 중간 단계를 거쳐 최종물질 제조 시 고순도의 9-페닐카바졸을 합성하여 본 발명을 완성하게 되었다.The present invention relates to the production of 9-phenylcarbazole, especially the compound of Formula 2 to the compound of Formula 1, without using an expensive palladium catalyst, and through a benzene intermediate step to produce high purity 9-phenylcarbazole in the final product. The present invention was completed by synthesizing the sol.
본 발명에 기재된 강염기는 유기합성 분야에서 통상적으로 사용되는 메탈 알콕사이드이면 모두 가능하나, 반응 효율면에서 바람직하게는 메탈 t-부톡사이드일수 있다 The strong base described in the present invention can be any metal alkoxide commonly used in the field of organic synthesis, but is preferably metal t-butoxide in terms of reaction efficiency.
본 발명에 기재된 할로벤젠은 브로모벤젠 또는 클로로벤젠이 가능하나, 반응 효율면에서 바람직하게는 클로로벤젠일 수 있다 The halobenzene described in the present invention can be bromobenzene or chlorobenzene, but is preferably chlorobenzene in terms of reaction efficiency.
본 발명에 따르는 상기 화학식 1로 표시되는 9-페닐카바졸의 제조는 용매를 추가하지 않거나 용매로 디메틸포름아마이드, 미메틸아세트아마이드, 또는 N-메틸피롤리돈을 9H-카바졸 대비 1:1 ~ 1:5 중량비로 추가할 수 있으며, 반응온도는 100℃ 내지 150℃에서 수행되는 것을 특징으로 하며, 반응 효율면에서 125℃ 내지 135℃의 온도에서 수행될 수 있다. In the preparation of 9-phenylcarbazole represented by Formula 1 according to the present invention, no solvent is added or dimethylformamide, mimethylacetamide, or N-methylpyrrolidone is used as a solvent in 1:1 ratio compared to 9H -carbazole. It can be added in a weight ratio of 1 to 1:5, and the reaction temperature is characterized as being carried out at 100°C to 150°C, and in terms of reaction efficiency, it can be carried out at a temperature of 125°C to 135°C.
본 발명의 제조방법에 따라 제조된 상기 화학식 1의 9-페닐카바졸의 제조에 있어서 유용한 중간체로 사용할 수 있으며, 이러한 9-페닐카바졸는 올레드 소재로 유용한 삼성 시피엘의 제조에 있어서 매우 중요한 중간체로 사용될 수 있다.It can be used as a useful intermediate in the production of 9-phenylcarbazole of Chemical Formula 1 prepared according to the production method of the present invention, and this 9-phenylcarbazole is a very important intermediate in the production of Samsung CPL, which is useful as an OLED material. can be used as
본 발명에 따른 9-페닐카바졸은 제조 과정에 있어서 팔라듐 촉매를 사용하지 않고, 더욱 바람직하게는 원-포트 반응을 통해 간단한 공정으로 고순도의 9-페닐카바졸을 수득할 수 있다는 효과를 가지게 된다.9-phenylcarbazole according to the present invention has the effect of obtaining high purity 9-phenylcarbazole in a simple process without using a palladium catalyst in the production process, more preferably through a one-pot reaction. .
또한 본 발명에 따라 제조된 9-페닐카바졸은 상이한 작용기를 가지는 9-페닐카바졸 유도체의 제조에 있어서 중간체로 사용할 수 있으며, 이러한 9-페닐카바졸 유도체는 올레드 소재로 유용한 삼성 시피엘의 제조에 있어서 매우 중요한 중간체로 사용될 수 있다.In addition, 9-phenylcarbazole prepared according to the present invention can be used as an intermediate in the production of 9-phenylcarbazole derivatives with different functional groups, and these 9-phenylcarbazole derivatives are used as Samsung CPL's product that is useful as an OLED material. It can be used as a very important intermediate in manufacturing.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 실시 예를 들어 상세하게 설명하겠는바, 본 발명에 따른 실시 예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 상술하는 실시 예들에 한정되는 것으로 해석 되어져서는 안된다. 본 발명의 실시 예들은 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해서 제공되어지는 것이다.Below, for a detailed understanding of the present invention, representative compounds of the present invention will be described in detail through examples. The embodiments according to the present invention may be modified into various other forms, and the scope of the present invention is as follows. It should not be construed as limited to the above-described embodiments. Embodiments of the present invention are provided to more completely explain the present invention to those with average knowledge in the art.
[실시예 1] 클로로벤제을 사용하는 9-페닐카바졸의 제조[Example 1] Preparation of 9-phenylcarbazole using chlorobenzene
클로로벤젠 446.71g(3.588mole, 6eq), 9H-카바졸 100g(0.598mole, 1eq) 을 300mL 디메틸포름아마이드가 투입된 반응기에 가하고 교반하면서 포타슘 t-부톡사이드 167.8g(1.495mole, 2.5eq) 을 서서히 첨가한다. 반응용액의 온도를 125±5℃에서 5시간 반응한다. HPLC로 반응 종결 확인 후 실온으로 냉각한다. 반응액에 정제수 900mL를 넣고 30분 교반하고 정치시켜 층 분리한다. 분리된 유기층은 진공 농축으로 용매를 제거하여 크루드 9-페닐카바졸을 수득한다. 얻어진 크루드 9-페닐카바졸에 메탄옥 200mL를 가하고 실온에서 4시간 교반 후 여과하여 목적 화합물인 9-페닐카바졸 81g(순도 99.6%)을 얻었다. 446.71g (3.588mole, 6eq) of chlorobenzene and 100g (0.598mole, 1eq) of 9 H -carbazole were added to the reactor containing 300mL dimethylformamide, and while stirring, 167.8g (1.495mole, 2.5eq) of potassium t-butoxide was added. Add slowly. React at the temperature of the reaction solution at 125±5℃ for 5 hours. After confirming the completion of the reaction by HPLC, cool to room temperature. Add 900 mL of purified water to the reaction solution, stir for 30 minutes, and let stand to separate the layers. The separated organic layer is vacuum concentrated to remove the solvent to obtain crude 9-phenylcarbazole. 200 mL of methanoce was added to the obtained crude 9-phenylcarbazole, stirred at room temperature for 4 hours, and filtered to obtain 81 g (purity 99.6%) of 9-phenylcarbazole, the target compound.
1H-NMR (400MHz,CDCl3)δ: 8.21(d, 1), 8.19(d, 1), 7.67~7.60(m, 4), 7.53~7.49(m, 1), 7.46(d, 2), 7.45(t, 2), 7.37~7.30(m, 1) 1 H-NMR (400MHz, CDCl 3 )δ: 8.21(d, 1), 8.19(d, 1), 7.67~7.60(m, 4), 7.53~7.49(m, 1), 7.46(d, 2) , 7.45(t, 2), 7.37~7.30(m, 1)
[실시예 2] 브로모벤젠을 사용하는 9-페닐카바졸의 제조[Example 2] Preparation of 9-phenylcarbazole using bromobenzene
브로모벤젠 623.12g(3.588mole, 6eq), 9H-카바졸 100g(0.598mole, 1eq) 을 300mL 디메틸포름아마이드가 투입된 반응기에 가하고 교반하면서 포타슘 t-부톡사이드 167.8g(1.495mole, 2.5eq) 을 서서히 첨가한다. 반응 용액의 온도를 125±5℃에서 5시간 반응한다. HPLC로 반응 종결 확인 후 실온으로 냉각한다. 반응액에 정제수 900mL를 넣고 30분 교반하고 정치시켜 층 분리한다. 분리된 유기층은 진공 농축으로 용매를 제거하여 크루드 9-페닐카바졸을 수득한다. 얻어진 크루드 9-페닐카바졸에 메탄옥 200mL를 가하고 실온에서 4시간 교반 후 여과하여 목적 화합물인 9-페닐카바졸 70g(순도 99.2%)을 얻었다.623.12g (3.588mole, 6eq) of bromobenzene and 100g (0.598mole, 1eq) of 9 H -carbazole were added to a reactor containing 300mL dimethylformamide and stirred while adding 167.8g (1.495mole, 2.5eq) of potassium t-butoxide. Add slowly. React at the temperature of the reaction solution at 125 ± 5°C for 5 hours. After confirming the completion of the reaction by HPLC, cool to room temperature. Add 900 mL of purified water to the reaction solution, stir for 30 minutes, and let stand to separate the layers. The separated organic layer is vacuum concentrated to remove the solvent to obtain crude 9-phenylcarbazole. 200 mL of methanoce was added to the obtained crude 9-phenylcarbazole, stirred at room temperature for 4 hours, and then filtered to obtain 70 g (purity 99.2%) of 9-phenylcarbazole, the target compound.
1H-NMR (400MHz,CDCl3)δ: 8.21(d, 1), 8.19(d, 1), 7.67~7.60(m, 4), 7.53~7.49(m, 1), 7.46(d, 2), 7.45(t, 2), 7.37~7.30(m, 1) 1 H-NMR (400MHz, CDCl 3 )δ: 8.21(d, 1), 8.19(d, 1), 7.67~7.60(m, 4), 7.53~7.49(m, 1), 7.46(d, 2) , 7.45(t, 2), 7.37~7.30(m, 1)
이상에서 살펴본 본 발명은 실시예들을 참고로 하여 설명하였으나 이는 예시적인 것에 불과하며 당해 분야에서 통상의 지식을 가진 자라면 이로부터 다양한 변형 및 실시예의 변형이 가능하다는 점을 이해할 것이다. 그러나, 이와 같은 변형은 본 발명의 기술적 보호범위 내에 있다고 보아야 한다. 따라서, 본 발명의 진정한 기술적 보호범위는 첨부된 청구범위의 기술적 사상에 의해서 정해져야 할 것이다.The present invention examined above has been described with reference to embodiments, but these are merely illustrative examples, and those skilled in the art will understand that various modifications and variations of embodiments are possible therefrom. However, such modifications should be considered within the technical protection scope of the present invention. Therefore, the true technical protection scope of the present invention should be determined by the technical spirit of the attached claims.
Claims (4)
[화학식 1]
[화학식 2]
[화학식 3]
[화학식 4]
[상기 화학식 1 내지 4에서,
X는 Br또는 Cl이며;
M은 Li, Na 또는 K이다.]
A method of producing 9-phenylcarbazole of Formula 1 by reacting a halobenzene compound of Formula 2 below with a strong base and then reacting with 9H-carbazole of Formula 3.
[Formula 1]
[Formula 2]
[Formula 3]
[Formula 4]
[In Formulas 1 to 4,
X is Br or Cl;
M is Li, Na or K.]
할로벤젠은 브로모벤젠 또는 클로로벤젠이 가능하나, 반응 효율면에서 바람직하게는 클로로벤젠일 수 있으며, 화학식 3의 카바졸 대비 2 내지 10당량을 사용하는 것을 특징으로 하는 9-페닐카바졸의 제조 방법.
According to paragraph 1,
Halobenzene can be bromobenzene or chlorobenzene, but is preferably chlorobenzene in terms of reaction efficiency, and is used in an amount of 2 to 10 equivalents compared to the carbazole of Formula 3. Production of 9-phenylcarbazole method.
상기 강염기는 리튬 t-부톡사이드, 소듐 t-부톡사이드 또는 포타슘 t-부톡사이드로부터 선택되는 것을 특징으로 하는 9-페닐카바졸의 제조 방법.
According to paragraph 1,
A method for producing 9-phenylcarbazole, wherein the strong base is selected from lithium t-butoxide, sodium t-butoxide, or potassium t-butoxide.
반응용매를 추가하지 않거나 용매로 디메틸포름아마이드, 미메틸아세트아마이드, 또는 N-메틸피롤리돈을 9H-카바졸 대비 1:1 ~ 1:5 중량비로 추가할 수 있으며, 반응온도는 100℃ 내지 150℃에서 수행되는 것을 특징으로 하며, 반응 효율면에서 125℃ 내지 135℃의 온도에서 수행되는 제조 방법.According to paragraph 1,
The reaction solvent may not be added, or dimethylformamide, mimethylacetamide, or N-methylpyrrolidone may be added as a solvent in a weight ratio of 1:1 to 1:5 relative to 9H-carbazole, and the reaction temperature is 100°C to 100°C. A manufacturing method characterized by being carried out at 150°C, and carried out at a temperature of 125°C to 135°C in terms of reaction efficiency.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004072088A2 (en) | 2003-02-14 | 2004-08-26 | Takasago International Corporation | Phosphine compound, intermediate, palladium-complex, and use thereof |
| US20070282111A1 (en) | 2006-06-06 | 2007-12-06 | Tosoh Corporation | Catalyst for producing arylamine and process for producing arylamine by means thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004072088A2 (en) | 2003-02-14 | 2004-08-26 | Takasago International Corporation | Phosphine compound, intermediate, palladium-complex, and use thereof |
| US20070282111A1 (en) | 2006-06-06 | 2007-12-06 | Tosoh Corporation | Catalyst for producing arylamine and process for producing arylamine by means thereof |
Non-Patent Citations (1)
| Title |
|---|
| Tetrahedron Letters (2000), 41(4), 481-483. |
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