Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 60811-21-4, name: 4-Bromo-2-chloro-1-fluorobenzene

To a solution of 4-bromo-2-chloro-1-fluorobenzene (5.00 g, 23.9 mmol) in THF (40 mL) was added lithium diisopropylamide (14.3 mL, 28.6 mmol) drop wise at -78 C. The resultant mixture was stirred at -78 C. for 2 h and then DMF (2.70 mL, 35.8 mmol) was added. The reaction mixture was warmed to room temperature, quenched with aq. NH4Cl, and extracted with EtOAc (3*100 mL). The combined organic layers were concentrated and purified by chromatography (0-10% EtOAc in petroleum ether) to give the title compound. 1H NMR (400 MHz, CDCl3) delta 10.27-10.33 (m, 1H), 7.56 (dd, J=8.6 Hz, 4.3 Hz, 1H), 7.18-7.26 (m, 1H).

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Reference:
Patent; Merck Sharp & Dohme Corp.; Lapointe, Blair T.; Fuller, Peter H.; Gunaydin, Hakan; Liu, Kun; Molinari, Danielle F.; Pu, Qinglin; Scott, Mark E.; Trotter, B. Wesley; Zhang, Hongjun; US2018/305320; (2018); A1;,
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Reference of 60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Bromo-2-chloro-1-fluorobenzene (720 mmol, 150.8 g), phenylboronic acid (792 mmol, 96.6 g), 2 M aqueous solution (360 ml) of potassium carbonate (1,080 mmol, 149.3 g), toluene (720 ml), and ethanol (144 ml) were added to a three-necked flask, and the flask was flushed with nitrogen. Tetrakis(triphenylphosphine) palladium(0) (Pd(PPh3)4(21.6 mmol, 21.6 g) was added thereto, and the reaction mixture was heated under stirring at a temperature 80 C. for 8 hours. The reaction mixture was cooled to room temperature, diluted with toluene (1 L), filtered by using celite, and washed twice with water by using a separatory funnel. The reaction mixture was dried by using anhydrous magnesium sulfate, filtered through a silica gel pad, and then, concentrated. The precipitated solid was purified by silica gel column chromatography (developing solvent hexane_toluene=7:3) and recrystallized in methanol to obtain Intermediate 3-1. The amount of Intermediate 3-1 obtained was 101.2 g and the yield of Intermediate 3-1 was 68%.

Statistics shows that 4-Bromo-2-chloro-1-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 60811-21-4.

Reference:
Patent; Samsung Electronics Co., Ltd.; INAYAMA, Satoshi; IRISA, Shiro; KORAI, Keisuke; SAKURAI, Rie; ITO, Mitsunori; NUMATA, Masaki; (265 pag.)US2019/214570; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14862-52-3, name is 3,5-Dibromochlorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 14862-52-3, Formula: C6H3Br2Cl

General procedure: Typically, TDPP (200 mg, 0.27 mmol), dibromobenzene derivatives 0.11 mmol, anhydrous Cs2CO3(200 mg, 0.61 mmol), PivOH (7.9 mg, 0.08 mmol), Pd2(dba)3 (4.00 mg, 1.5 mol%), tris(o-methoxyphenyl)phosphine (3.08 mg, 3 mol%) were successively added into a Schlenk tube. The tube was purged by three repetitions of vacuum and argon filling. Then, 5 mL anhydrous toluene was added via syringe.The reaction solution was deoxygenated using three freeze-vacuum-thaw cycles, and then rigorouslystirred at 100 C for 24 h under argon atmosphere. Removal of the toluene by rotary evaporatoraorded the crude product, which was then purified by chromatogragh column (CC) on silica gelusing a mixture of CH2Cl2 and hexane as eluent, giving the target molecules Ms1~9.

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Reference:
Article; Liu, Hui; Zhang, Xiao-Feng; Cheng, Jing-Zhao; Zhong, Ai-Guo; Wen, He-Rui; Liu, Shi-Yong; Molecules; vol. 24; 9; (2019);,
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89794-02-5, name is 4-Bromo-2-chlorotoluene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H6BrCl

General procedure: 10.0 mmol of the specified boronic ester (I; R1), 30.0 mmol of magnesium turnings and 10.0 mmol of the salt (II) were suspended in a mixture of 3.40 g of anhydrous toluene and 0.73 g of anhydrous tetrahydrofuran in a dry four-neck flask with a mechanical stirrer, thermometer, metal condenser and pressure-equalized dropping funnel under a nitrogen atmosphere, and stirred vigorously for 30 min. The appropriate haloaromatic (III, R4) was added to this solution, at first in undiluted form, until the onset of exothermicity signals the start of the reaction. The remaining total amount of 30.6 mmol of haloaromatic was diluted with 10.0 g of anhydrous toluene and 10.0 g of anhydrous tetrahydrofuran and added dropwise at such a rate that the internal temperature does not exceed 45 C. On completion of addition, the reaction mixture was heated at reflux for 1 h or until the dissolution of the magnesium was complete. The resulting suspension was discharged onto 50 g of ice-water, and the resulting solids are isolated, washed with cold water and dried under reduced pressure. Examples 15, 18, 20 and 27 and 46-52 were extracted from the aqueous phase with 100 ml of ethyl acetate, the solvent was distilled off under reduced pressure and the resulting oils were isolated. The isolated yield for Example 1 that was prepared by this method was 2.87 g (72% of theory), whereas Example 1 prepared according to DE 198 50 139 A1 was obtained in a yield of 47% of theory.The composition of Examples 1-76 and selected physical properties are summarized in Table 2.

The synthetic route of 89794-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Covestro Deutschland AG; ROeLLE, Thomas; BERNETH, Horst; HOeNEL, Dennis; BRUDER, Friedrich-Karl; (34 pag.)US2019/276479; (2019); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 61881-19-4 as follows. Application In Synthesis of 2,2,2-Trifluoro-N-phenylacetimidoyl chloride

4.3 3,4-Di-O-benzoyl-2-O-triisopropylsilyl-alpha-L-fucopyranosyl N-phenyltrifluoroacetimidate (6) To a solution of 3,4-di-O-benzoyl-2-O-triisopropylsilyl-L-fucopyranose (5) (0.25?g, 0.5?mmol) in CH2Cl2 (3.5?mL) CF3C(NPh)Cl [ 94 ] (0.37?mL, 2.2?mmol) and Cs2CO3 (290?mg, 0.9?mmol) were added at 0?C. The reaction mixture was stirred at 20?C for 20?h. Then the mixture was diluted with CHCl3 (50?mL), organic layer was separated and washed with H2O (50?mL), concentrated under reduced pressure and the residue dried in vacuo and purified by silica gel column chromatography (petroleum ether-EtOAc, 10:1???3:1) to give imidate 6 as a white foam (310?mg, 93%). [alpha]D23 -167.0 (c 1.0, CHCl3). Rf?=?0.71 (petroleum ether-EtOAc, 4:1). 1H NMR (300?MHz, CDCl3, delta, ppm, J, Hz): 0.73-1.10 (m, 21H, (CH3)2CH), 1.31 (d, 3H, J6,5 6.5, H-6), 4.50 (q, 1H, J5,6 6.5, H-5), 4.77 (dd, 1H, J2,1 3.5, J2,3 10.2, H-2), 5.70-5.85 (m, 2H, H-3, H-4), 6.58 (br.s, 1H, H-1), 6.80-6.95 (m, 2H, PhN (H-2, H-6)), 7.08-7.20 (m, 1H, PhN (H-4)), 7.24-7.40 (m, 4H, Ph), 7.46-7.57 (m, 3H, Ph), 7.59-7.70 (m, 1H, PhCO (H-4)), 7.78-7.87 (m, 2H, PhCO (H-2, H-6)), 8.04-8.15 (m, 2H, PhCO (H-2, H-6)). 13C NMR (75?MHz, CDCl3, delta, ppm, J, Hz): 12.4 ((CH3)2CH), 16.1 (C-6), 17.75, 17.78 ((CH3)2CH), 67.2 (C-2), 67.6 (C-5), 71.6, 71.7 (C-3 C-4), 95.4 (C-1), 116.2 (q, J 286.8, CF3), 119.4 (PhN (C-2, C-6)), 124.2 (PhN (C-4)), 128.1 (Ph (C-3, C-5)), 128.5 (Ph (C-3, C-5)), 128.7 (Ph (C-3, C-5)), 129.45 (PhCO (C-1)), 129.54 (PhCO (C-2, C-6)), 129.73 (PhCO (C-1)), 129.76 (PhCO (C-2, C-6)), 133.0, 133.4 (PhCO (C-4)), 143.6 (q, J 35.4, CF3C=N), 143.7 (PhN (C-1)), 165.67, 165.73 (CO). HRESIMS: found m/z 722.2729 [M+Na]+. Calcd for C37H44F3NNaO7Si: 722.2731. Found m/z 738.2468 [M+K]+. Calcd for C37H44F3KNO7Si: 738.2471.

According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abronina, Polina I.; Zinin, Alexander I.; Romashin, Denis A.; Tereshina, Valeria V.; Chizhov, Alexander O.; Kononov, Leonid O.; Carbohydrate Research; vol. 464; (2018); p. 28 – 43;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 172921-33-4, name is 1-Bromo-4-chloro-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H2BrClF2

Under nitrogen, 1-bromo-4-chloro-2,5-difluorobenzene (12 g, 52.8 mmol),(2-methoxyphenyl) boronic acid (8.42 g, 55.4 mmol), and potassium carbonate (14.58 g, 106 mmol)Is dissolved in a mixture of toluene (100 ml) / water (20 ml),A colorless suspension was obtained. Tetrakis (triphenylphosphine) palladium (0) (0.544 g, 0.528 mmol)Was added to the reaction mixture all at once. Degas the reaction mixture,Heated to reflux under nitrogen for 16 hours.According to the results of gas chromatograph mass spectrometry (GCMS) analysis, the reaction was not completed. Therefore,> 7 g boronic acid as catalyst, 1 g K2CO3,And 0.6 g of Pd (PPh3) 4,The resulting mixture was degassed and refluxed for 14 hours under nitrogen.The reaction mixture is then cooled, the organic phase is separated off and evaporated,Purify by silica gel column chromatography eluting with heptane as a yellow oil,4-Chloro-2,5-difluoro-2′-methoxy-1,1′-biphenyl was obtained.(11.0 g, 82% yield).

The synthetic route of 172921-33-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; Zhiqiang, Ji; Jui Yi, Tsai; Alexey, Borisovich Dyatkin; Chun, Lin; (197 pag.)JP2019/127489; (2019); A;,
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Reference of 933190-51-3, A common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A microwave vial was charged with a mixture of 8-bromo-6- chloroimidazo[l,2-b]pyridazine (1.06 g, 4.56 mmol), 3-(l,3,2-dioxaborinan-2-yl)pyridine (0.743 g, 4.56 mmol), dioxane (14 mL), and tetrakis(triphenylphosphine)palladium(0) (0.527 g, 0.456 mmol), and K3P04 (2.90 g, 13.68 mmol) (2.0 M water solution) was stirred at room temperature for 5 min. under nitrogen. The resulting mixture was heated to 100 C for 8 h in microwave. The reaction mixture was cooled to room temperature, quenched with water, and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3 X 20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2S04, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by BIOTAGE (20-60% EtOAc/hex, 1.5 L) to the product (0.39 g, 37%). LC/MS: Rt = 1.07 min. LC/MS (Condition A): 231.09/233.09.

The synthetic route of 933190-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; LIU, Peiying; BALOG, James Aaron; WO2011/137155; (2011); A1;,
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Application of 174913-10-1, The chemical industry reduces the impact on the environment during synthesis 174913-10-1, name is 1-Bromo-3-chloro-2-methoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 217 7-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl) 3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H). This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91%) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-3-chloro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 60811-18-9 as follows. Recommanded Product: 60811-18-9

A] stirred solution of 4-bromo-1- chloro-2-fluorobenzene (25g, 0. 119mol) and triisopropylborate (30. 5ml, 0.131 mol) in dry THF [(500ML)] under argon is cooled [TO-100C] and n-butyllithium (52. [5ML] of a 2.5M solution in hexanes, 0.131 mol) is added dropwise over [15MIN.] The reaction mixture is allowed to warm gradually to room temperature over 18h before it is quenched by the addition of 2M hydrochloric acid (250ml) and stirred at room temperature overnight. The THF is removed under reduced pressure, the aqueous residue is diluted with water [(500ML)] and the mixture is extracted with diethyl ether (3 x [200ML).] The combined ether extracts are washed with saturated brine [(200MOI),] dried [(MGS04),] filtered, evaporated and [DRIED IN VACUO TO] give a colourless solid-a mixture of 4-Chloro-3-fluorobenzeneboronic acid and the functionally equivalent [CYCLOTRIBOROXANE.]

According to the analysis of related databases, 60811-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/33435; (2004); A1;,
Chloride – Wikipedia,
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Related Products of 85462-59-5,Some common heterocyclic compound, 85462-59-5, name is 2-Bromo-5-chloro-4-fluoroaniline, molecular formula is C6H4BrClFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2: 2-bromo-5-chloro-4-fluoro-N,N-dimethylaniline 2-Bromo-5-chloro-4-fluoroaniline (2.25 g, 0.01 mol), 40% formaldehyde solution (10 mL, 0.133 mol), and formic acid (4.6 g, 0.1 mol) were reacted at 100C for 3 hours. NaOH was added to adjust it to strongly alkaline, and then the resultant was extracted with CH2Cl2. The extract was dried, spin evaporated, and purified by silica gel column chromatography to give 2-bromo-5-chloro-4-fluoro-N,N-dimethylaniline (2.46 g, 97% yield). 1H-NMR (400 MHz, CDCl3):delta= 7.368 (d, J = 8.4 Hz, 1H), 7.079 (d, J = 6.8 Hz, 1H), 2.748 (s, 6H). MS m/z [ESI]: 253.9 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-chloro-4-fluoroaniline, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XIAO, Dengming; XU, Xinhe; LIU, Xijie; HU, Yuandong; YU, Honghao; LIU, Zhihua; PENG, Yong; SUN, Yinghui; LUO, Hong; KONG, Fansheng; HAN, Yongxin; SUN, Jian; EP2952510; (2015); A1;,
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