1-Bromodibenzo[b,d]furan CAS 50548-45-3 compound is a very important intermediate of medicine and photoelectric materials found at present, and is a key core structure with very high use frequency in the research and development of medicine and photoelectric materials.

2-Chloro-4 - (naphthalene [2,1-B] benzofuran-9-yl) quinazoline is a cyclic mechanism, but its state is not very active, and other benzene ring positions have been fully stained, so the next stage of product can only be completed by replacing Cl element. Compared with Cl element, N element is more stable in nature and is not easy to be replaced. It has more strict requirements for replacement and higher requirements for reaction environment.

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Name	CAS No.	Molecule Formula	Molecular Weight	Elemental Analysis	QTY/g
2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine		C27H16ClN3O	434	C74.74; H3.72; Cl8.17; N9.68; O3.69	101
10-bromobenzo[b]naphtho[1,2-d]furan	1256544-20-3	C16H9BrO	297	C64.67; H3.05; Br26.89; O5.38	27
12H-benzofuro[2,3-a]carbazole	1338919-70-2	C18H11NO	257	C84.03; H4.31; N5.44; O6.22	39
2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine	1883265-32-4	C21H12ClN3O	358	C70.50; H3.38; Cl9.91; N11.74; O4.47	92
4-(5''-chloro-[1,1':3',1'':3'',1'''-quaterphenyl]-5'-yl)dibenzo[b,d]furan		C36H23ClO	507	C85.28; H4.57; Cl6.99; O3.16	509
Dibenzofuran, 1-bromo-4-chloro-	2252237-87-7	C12H6BrClO	282	C51.20; H2.15; Br28.38; Cl12.59; O5.68	0
11-bromospiro[benzo[c]fluorene-7,9'-xanthene]		C29H17BrO	461	C75.50; H3.71; Br17.32; O3.47	602
naphtho[2,3-b]benzofuran-1-ylboronic acid	2261008-21-1	C16H11BO3	262	C73.33; H4.23; B4.12; O18.31	0
2-(10-phenylanthracen-9-yl)benzo[d]naphtho[2,3-b]furan		C36H22O	471	C91.89; H4.71; O3.40	0
1-bromo-7-chlorodibenzo[b,d]furan	2173555-52-5	C12H6BrClO	281	C51.20; H2.15; Br28.38; Cl12.59; O5.68	72
2-chloro-4-(naphtho[2,1- b]benzofuran-9-yl)quinazoline	1869142-01-7	C24H13ClN2O	381	C75.69; H3.44; Cl9.31; N7.36; O4.20	100
1-(7-chlorodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine		C27H18ClN3O	436	C74.40; H4.16; Cl8.13; N9.64; O3.67	93
Dibenzofuran, 1-bromo-4-phenyl-	1821235-69-1	C18H11BrO	323	C66.90; H3.43; Br24.72; O4.95	200
1-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro-, benzo[b]naphtho[1,2-d]furan-3-yl ester	2130009-91-3	C20H9F9O4S	516	C46.52; H1.76; F33.12; O12.39; S6.21	0
3-Chloro-5,5-dimethyl-5Hbenzo[b]benzo[4,5]silolo[2,3-g]benzofuran		C20H15ClOSi	335	C71.73; H4.52; Cl10.59; O4.78; Si8.39	82
11-bromo-benzo [b] naphtho [1,2-d] furan	1898210-08-6	C16H9BrO	297	C64.67; H3.05; Br26.89; O5.38	61
Spiro[11H-benzo[b]fluorene-11,9'-[9H]xanthene], 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-	2192307-05-2	C35H29BO3	508	C82.68; H5.75; B2.13; O9.44	0
2-chlorospiro[fluorene-9,9'-xanthene]-7-carbonitrile	2259843-42-8	C26H14ClNO	392	C79.69; H3.60; Cl9.05; N3.57; O4.08	79
dibenzo[b,d]furan-1-amine	50548-40-8	C12H9NO	183	C78.67; H4.95; N7.65; O8.73	450
1-bromo-8-chlorodibenzo[b,d]furan	2173554-83-9	C12H6BrClO	282	C51.20; H2.15; Br28.38; Cl12.59; O5.68	0

The invention relates to 1-bromodibenzofuran and a synthesis method thereof, which comprises the following steps:

step 1)

Reacting m-fluorobromobenzene, trimethyl borate and diisopropyl lithium amino to generate 2-bromo-6-fluorophenylboronic acid at low temperature;

Step 2)

Using the 2-bromo-6-fluorophenylboronic acid generated in step 1) and potassium difluorohydrogen to generate potassium 2-bromo-6-fluorophenyl trifluoroborate through salifying reaction;

Step 3)

The 2 bromo 6 fluorophenyl potassium trifluoroborate generated in step 2) and o-bromophenol undergo coupling reaction to generate 2 'bromo 6' fluorobiphenyl 2 alcohol;

Step 4)

The 2 'bromo 6' fluorobiphenyl 2 alcohol generated in step 3) generates 1 bromodibenzofuran through ring closing reaction.

A preparation method of 2 chloro 4,6-diphenyl-1,3,5 triazine. In this method, 1,3,5 triazine and phenylboronic acid were used as starting materials, and nickel phosphine complex was used as catalyst to produce 2 chloro 4,6 diphenyl 1,3,5 triazine in one step reaction. This method is simple in process, convenient in operation, mild in reaction conditions, good in selectivity, and can quantitatively generate disubstitutes. It overcomes the shortcomings of poor selectivity of Friede1 Crafts alkylation method, avoids the pressure of anhydrous aluminum trichloride catalyst on the treatment of three wastes, and meets the requirements of green environmental protection.

Applications

1-Bromodibenzo[b,d]furan is an important organic compound, and as one of the derivatives of dibenzofuran, its unique molecular structure and physicochemical properties make it widely used in multiple fields. The following will elaborate on the uses of 1-bromodibenzofuran in the fields of medicine, pesticides, dyes, electronic materials, and more.

1-Bromodibenzo[b,d]furan uses | Shaanxi BLOOM Tech Co., Ltd

Application in the field of medicine

1. Pharmaceutical intermediates

Drug synthesis: 1-Bromodibenzofuran is an important intermediate in the synthesis of various drugs, which can be used for the synthesis of anticancer drugs, antibacterial drugs, etc. Its unique molecular structure makes it play an important role in drug synthesis.
Laboratory research and development: In the process of drug development, 1-bromodibenzofuran is often used as a model compound or reaction material to help researchers explore new drug synthesis routes and reaction mechanisms.

2. Pharmacological effects

Potential pharmacological activity: Although 1-bromodibenzofuran itself may not be directly used as a drug, its derivatives or analogues may have pharmacological activities such as anti-tumor, anti-inflammatory, etc. Therefore, it has potential application value in drug discovery and development.
3. Regulations and standards

In the pharmaceutical field, the use of 1-bromodibenzofuran should comply with relevant regulations and standards to ensure the safety and efficacy of the drug.

Application in the field of pesticides

1. Pesticide intermediates

Pesticide synthesis: 1-bromodibenzofuran can be used to synthesize various insecticides, and its unique molecular structure gives insecticides better insecticidal effects and longer shelf life.
Synthesis of fungicides: In the synthesis of fungicides, 1-bromodibenzofuran also plays an important role. Its derivatives or analogues can be used to prevent and control various plant diseases, improve crop yield and quality.

2. Antibacterial effect

Prevention and control of plant diseases: Studies have shown that dibenzofuran compounds have good antibacterial effects on plant diseases such as root rot and bacterial wilt. Therefore, 1-bromodibenzofuran has potential application value in the field of pesticides.
3. Regulations and standards

In the field of pesticides, the use of 1-bromodibenzofuran should comply with relevant regulations and standards to ensure the safety and effectiveness of the pesticide, while reducing its impact on the environment and ecology.

Application in the field of dyes

1. Dye intermediates

High performance dye synthesis: 1-bromodibenzofuran can be used to synthesize high-performance dyes, and its unique molecular structure endows the dyes with good color fastness and vividness.
Improving dye quality: By introducing 1-bromodibenzofuran structure, the light resistance, washing resistance, sweat resistance and other properties of dyes can be significantly improved, meeting the market's demand for high-quality dyes.

2. Application of dyes

Textile printing and dyeing: In the textile printing and dyeing industry, the use of dyes containing 1-bromodibenzofuran structures can give textiles more vibrant and long-lasting colors.
Other fields: In addition to textile printing and dyeing, these dyes can also be used in plastics, inks, and other fields to enhance the color performance of products.
3. Regulations and standards

In the field of dyes, the use of 1-bromodibenzofuran should comply with relevant regulations and standards to ensure the safety and environmental friendliness of dyes.

Application in the field of electronic materials

1. Application of electronic devices

Display screen: In the field of display screens, the use of organic luminescent materials containing 1-bromodibenzofuran structure can produce more efficient, energy-saving, and brightly colored display screens.
Other electronic devices: In addition to display screens, these materials can also be used in other electronic devices such as lighting and sensors to enhance the performance and quality of the devices.
2. Regulations and standards

In the field of electronic materials, the use of 1-bromodibenzofuran should comply with relevant regulations and standards to ensure the safety and reliability of the material.

1-Bromodibenzofuran, as a multifunctional organic compound, has broad application prospects in fields such as medicine, pesticides, dyes, and electronic materials. Its unique molecular structure and physicochemical properties make it have unique application value in different fields. With the continuous development of technology, the application fields of 1-bromodibenzofuran will continue to expand, providing more possibilities for the development of various industries.

Manufacturing Information

1-Bromodibenzo[b,d]furan based optoelectronic materials have a wide range of applications in blue organic light-emitting devices, and their development and research value is high. However, 1-bromodibenzofuran, as an important intermediate, has a low overall yield and a long process route in the synthesis of existing technologies, resulting in high costs. During the reaction process, waste gas and wastewater are generated, which are highly polluting and dangerous. The equipment requirements are high, and the post-treatment is complex, leading to a long production cycle.

Conventional Route 1

The overall yield of conventional line 1 is 38.4%, with a cost of around 12000 yuan. The third step of the process uses boron tribromide, which generates a large amount of hydrogen bromide gas during the post-treatment process, with intense heat release and the production of acid water. This causes significant equipment loss and poses a major safety hazard; The post-processing of this process is relatively complex, resulting in a long time. Taking the production of 3kg as an example, this process takes 20 days.

Conventional Route 2

The overall yield of conventional route 2 is 41%, with a cost of around 18000 yuan. The resulting product has a heavy pigment and is difficult to purify to 99% purity. This process has five steps, taking 3kg as an example, with a cycle of 23 days, and involves diazonium salt reaction, which poses certain risks to the operation. The methods reported in current literature have complex processes and high post-treatment pollution, therefore, the development of simple and green synthesis methods is of great significance.

Specific method:
Step 1) Use m-fluorobromobenzene, trimethyl borate, and diisopropylammonium lithium to undergo low-temperature reaction to generate 2-bromo-6-fluorophenylboronic acid, where the molar ratio of m-fluorobromobenzene, trimethyl borate, and diisopropylammonium lithium is 1-1.5:1 to 2:1 to 1.5;

Step 2) Use the 2-bromo-6-fluorophenylboronic acid and potassium difluorohydride generated in step 1) to undergo a salt formation reaction to produce potassium 2-bromo-6-fluoro-phenyltrifluoromethoborate, where the molar ratio of 2-bromo-6-fluorophenylboronic acid to potassium difluorohydride is 1:3-5;

Step 3) The potassium 2-bromo-6-fluoro-phenyltrifluoroborate generated in Step 2) undergoes a coupling reaction with ortho bromophenol to form 2 '- bromo-6' - fluorobiphenyl-2-ol, wherein the molar ratio of potassium 2-bromo-6-fluoro-phenyltrifluoroborate to ortho bromophenol is 1:1 to 1.3;

Step 4) The 2 '- bromo-6' - fluorobiphenyl-2-ol generated in Step 3) undergoes cyclization reaction to produce 1-bromodibenzofuran.

Preferably, the specific reaction steps of step 1) are as follows: under nitrogen protection, tetrahydrofuran is added to the reaction kettle, followed by diisopropylammonium lithium, and stirred to cool down to -78 ℃. Then, a tetrahydrofuran solution of m-fluorobromobenzene is added dropwise, and a large amount of solid precipitates after complete dropwise addition. The mixture is kept at -78 ℃ for 1-2 hours, and then trimethyl borate is added dropwise. After dripping, the system is clarified and naturally allowed to rise to room temperature to complete the reaction. Finally, at 50 ℃, tetrahydrofuran is evaporated under reduced pressure, and the remaining reaction solution is poured into a prepared dilute hydrochloric acid aqueous solution, stirred for 1 hour. A large amount of white solid precipitates, filtered, and a filter cake is obtained. Then, petroleum ether is used for hot pulping at 50 ℃ for 0.5 hours. Then, it was cooled to room temperature and filtered to obtain 1-Bromodibenzo[b,d]furan .

The preferred molar ratio of m-fluorobromobenzene, trimethylborate, and diisopropylammonium lithium is 1:1.2:1.

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