Tag: M.W=200-300

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H7BrFN

solution of [(4-bromo-2-fluorophenyl)methyl]amine (2.Og, 9.8mmol) and triethylamine (2.73ml, 19.6mmol) in dimethylformamide (20ml) was treated with 3- chloropropanesulfonyl chloride (1.74g, 9.8mmole) dropwise over 10 minutes with stirring under argon. This mixture was stirred for 30 minutes before being treated with sodium hydride (60% suspension in mineral oil, 1.176g, 29.4mmol) portionwise and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated under reduced pressure. Sample was then purified by column chromatography on silica using 10 to 90% ethyl acetate in n-pentane to afford the title compound as an oil (1.7g, 55%).LC/MS (ES): Found 308 & 310 (ES+), retention time 2.73mins. Ci0H11 BrFNO2S requires 307 & 309.1H-NMR (400MHz, CDCI3): 2.34 (2H, m), 3.19 (4H, m), 4.20 (2H, d, J=I Hz), 7.22-7.35 (3H, m).

The synthetic route of 112734-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/110566; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, belongs to bromides-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 314084-61-2, name: 2-Bromo-1,3-diethyl-5-methylbenzene

Under a nitrogen atmosphere and at normal pressure, 14 g of malonic acid dinitrile dissolved in 7 ml of 1-methyl-2-pyrrolidone are added dropwise in the course of 30 minutes, at from 20 to 25C, to a mechanically stirred mixture of 64 g of sodium carbonate in 200 mi of 1-methyl-2-pyrrolidone. The reaction mixture is heated to 100C and 45.5 g of 2-bromo- 1, 3-diethyl-5-methylbenzene are added, after which the mixture is heated to 120C. At that temperature, a mixture of 0.26 g of TRIPHENYLPHOSPHINE, 0.21 g of a commercially available palladium (LI) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.071 g of PALLADIUM (II) CHLORIDE in 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-methyl-2-pyrrolidone is added. The reaction mixture is stirred for from 2 to 3 hours at from 125 to 140C. A gas chromatogram of a sample (1 ml of reaction mixture partitioned between 2 ML of 1 N hydrochloric acid and 2 ml of tert-butyl methyl ether) shows that the product (2-(2, 6-DIETHYL-4-METHYLPHENYL) MALONIC acid dinitrile) has not formed.

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Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
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Reference of 61613-22-7, These common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, 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.

33 g (145 mmol) of di-tert-butyl dicarbonate first fill in 600 mL of toluene. To this solution 27g (110 mmol) of (2-bromophenyl)phenylamine and 1.3 g (11 mmol) of 4-dimethylaminopyridine, The mixture is boiled under reflux for 40 h. Subsequently 200mL of water was added to the reaction and separating the organic phase, the solvent was removed under reduced pressure. The residue was then recrystallized from hot hexane. Yield: 36 g (103 mmol), 95%.

Statistics shows that 2-Bromo-N-phenylaniline is playing an increasingly important role. we look forward to future research findings about 61613-22-7.

Reference:
Patent; Merck Patent GMBH; Farrahm, Amir Hossain; Flume, Christoph; Everille, Thomas; Yatsi, Anya; Montenegra, Elvira; Krober, Jonas Valentine; Rinke, Roophen; (59 pag.)KR2016/27155; (2016); A;,
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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. 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine, A new synthetic method of this compound is introduced below., name: 2,5-Dibromobenzene-1,4-diamine

Add a solution of peroxytrifluoroacetic acid in the reaction vessel, lower the temperature to -5 to 5 C, add 797.8 g (3mol) of 2,5-dibromo-p-aminoaniline, and keep the reaction at -5 to 5 C with stirring for 6 hours. After the reaction is complete, Add 2L of water, stir, and let stand. The organic layer was washed with 2L of saturated sodium bisulfite solution, 2L of saturated sodium bicarbonate solution, and water to pH 7-8. The solvent was distilled off under reduced pressure, and dichloromethane and methanol were used. The volume ratio of dichloromethane and methanol is 1: 2) The solution was recrystallized to obtain the product as a yellow solid 782.2 g of 2,5-dibromo-p-nitronitrobenzene (yield 80%).

The synthetic route of 25462-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing Pharmaceutical College; Liu Dianqing; He Dongxian; Wang Kun; Guo Shengchao; Wang Guangming; (7 pag.)CN110330432; (2019); A;,
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These common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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. Application In Synthesis of 3-Bromophenethylamine

2-(3-Bromo-phenyl)-ethylamine (0.5 mmol) and formaldehyde (0.42 mmol) were mixed in 3 ml of 1,2-dichloroethane in a process vial, which was sealed with a septum. Sodium triacetoxyborohydride (0.84 mmol) was added under argon atmosphere. The suspension was subjected to microwave irradiating conditions (CEM Discover equipped with a CEM Explorer automated reaction handling module). The reaction mixture was heated for 5 min at 90C and then cooled. The crude was evaporated to dryness and then suspended in aqueous NaHCO3. The product was extracted with CH2Cl2 and washed with aqueous NaHCO3. The CH2Cl2 extract was dried with anhydrous Na2SO4, filtered and evaporated to dryness to give the crude product [2-(3-bromo-phenyl)-ethyl]-methyl-amine. The crude was purified by flash column chromatography (CH2Cl2-MeOH as eluents) by using a CombiFlash Companion system to yield the title compound (75%) as colourless oil.

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

Reference:
Patent; Laboratorios del Dr. Esteve S.A.; EP1935886; (2008); A1;,
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Some common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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. Formula: C8H10BrN

To a stirred solution of commercially available1-(2-bromophenyl)-N-methylmethanamine (565 mg, 2.8 mmol, 1.0 equiv.) and propiolic acid (0.21 mL,3.4 mmol, 1.2 equiv.) in CH2Cl2 (30 mL) was added DCC (700 mg, 3.4 mmol, 1.2 equiv.) at 0 C.Then, the reaction temperature was raised to r.t. After 1.5 h, the reaction mixture was diluted withCH2Cl2 (200 mL), and then washed with aq. 2N-HCl (5 mL) and sat. aq. NaHCO3 (20 mL). The organiclayer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue waspurified by column chromatography (silica gel, hexanesEtOAc 3:1) to yield 6c (675 mg, 95% yield) asan off-white solid; m.p. = 53.1 C; Rf = 0.3 (silica gel, hexanesEtOAc 2:1); IR (film) 3283, 3215, 3061,2926, 2107, 1644, 1401 cm-1; 1H-NMR (CDCl3, 1.3:1 atropisomeric mixture): delta = 7.59 (d, J = 8.0 Hz,1H, major), 7.56 (d, J = 8.0 Hz, 1H, minor), 7.35 (t, J = 7.5 Hz, 1H, major), 7.30 (t, J = 7.5 Hz, 1H, minor),7.19 (t, J = 7.8 Hz, 2H, major), 7.16 (d, J = 7.8 Hz, 2H, minor), 4.91 (s, 2H, major), 4.75 (s, 2H, minor),3.09 (s, 1H, major), 3.20 (s, 1H, minor), 2.94 (s, 3H, major), 3.18 (s, 3H, minor), ppm; 13C-NMR (CDCl3): delta= 154.4 (major), 154.2 (minor), 135.3 (major), 135.3 (minor), 133.5 (major), 133.3 (minor), 129.8 (major),129.6 (minor), 129.5 (minor), 128.4 (major), 128.3 (major), 128.2 (minor), 80.0 (minor), 79.4 (major),76.0 (minor), 75.9 (major), 54.9 (major), 50.0 (minor), 36.5 (minor), 32.7 (major) ppm; HRMS (EI): calcd. forC23H18ClNO [M+]: 250.9946, found 250.9944.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 698-19-1, its application will become more common.

Reference:
Article; Park, Sunhwa; Lee, Jiyun; Shin, Kye Jung; Oh, Euichaul; Seo, Jae Hong; Bunce, Richard A.; Molecules; vol. 22; 3; (2017);,
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Synthetic Route of 937046-98-5,Some common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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.

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was placed a solution of compound 2a (3.2 g, 15.02 mmol) in THF (40 mL). n-Butyllithium (18.75 mL, 1.6 N in THF) was added dropwise at -78C, and then chloro[2-(chlorodimethylsilyl)ethyl]dimethylsilane (3.2 g, 14.87 mmol) was added at -78 C. After the resulting solution was stirred for 0.5 hours at -78 C, n- butyllithium (6.25 mL, 1.6 N in THF) was added. After the resulting mixture was stirred for 5 minutes, a solution of compound lh (3.7 g, 9.75 mmol) in THF (10 mL) was added to the mixture and the resulting solution was stirred for 2 hours at -78C. After that the reaction was quenched by the addition of 30 mL saturated aqueous solution of ammonium chloride, extracted with ethyl acetate (3×150 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 :20~1 :3) to provide 350 mg (7%) of compound 2c as an off-white solid. LC-MS: (ES, m/z): 514.0 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GIRIJAVALLABHAN, Vinay; BOGEN, Stephane; PAN, Weidong; DANG, Qun; DAVIES, Ian; WO2014/59901; (2014); A1;,
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Some common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, molecular formula is C7H7BrFN, 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. Quality Control of 5-Bromo-4-fluoro-2-methylaniline

(1 ‘-bis(diphenylphosphino)ferrocene)-dichioropalladium(il) (234 mg, 0,286 mmol), phenylboronic acid (907 mg, 7.44 mmol) and 5-bromo-4-fluoro-2-methylaniline (1.17 g, 5.72 mmol) were dissolved in DME (10 ml). Sodium carbonate aq 2M (5.7 mL, 1 1 mmol) was added, and the mixture was irradiated with microwaves for 2h at 120C. After removing the DME under reduced pressure, the residue was taken with AcOEt (15 mL) and washed with brine (2 x 10 mL). The organic layer was concentrated under reduced pressure and the residue was purified by semi-preparative HPLC-UV, to afford 6-fluoro-4-methyl-[1 ,1 ‘-biphenyl]-3-amine (812 mg, Y = 70%) as a dark oil. MS (ESI+) m/z: 202.1 [M+H]+. (0152) Starting from 6-fluoro-4-methyl-[1 , 1 ‘-biphenyl]-3-amine (751 mg, 3.73 mmol), 3- bromo-N-(6-fluoro-4-methyl-[1 ,1’-biphenyl]-3-yl)benzenesulfonamide was synhesized as described in Procedure B, affording a mixture of mono- and di-sulfonamide, which by hydrolysis with NaOH aq/Dioxane was completely converted to the mono- sulfonamide (1 .41 g, Y = 89%). MS (ESI+) m/z: 442.0 [M+Na]+. (0153) The sulfonamide (1 .03 g, 2.46 mmol) was then coupled with hept-6-ynoic acid (0.63 mL, 4.92 mmol) as described in Procedure B, to afford 7-(3-(N-(6-fluoro-4-methyl- [1 ,1 ‘-biphenyl3-3-yl)sulfamoyl)phenyl)hept-6-ynoic acid (290 mg, Y = 25%). MS (ES+) m/z: 466.2 [M+H]+. (0154) Compound 9 was then obtained by reduction of the alkyne derivative (290 mg, 0.623 mmol) as described for compound 2, as a white solid (235 mg, Y = 80%). 1H NMR (300 MHz, CHLOROFORM-cf) delta ppm 1.20 – 1.33 (m, 4 H) 1 .47 – 1.59 (m, 4 H) 2.01 (s, 3 H) 2.31 (t, J=7.34 Hz, 2 H) 2.58 (t, J=7.56 Hz, 2 H) 6.88 (d, J=10.96 Hz, 1 H) 7.00 (s, 1 H) 7.27 (d, J=7.45 Hz, 1 H) 7.32 – 7.43 (m, 7 H) 7.51 – 7.60 (m, 2 H). MS (ESI+) m/z: 470.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 627871-16-3, its application will become more common.

Reference:
Patent; DOMPE’ FARMACEUTICI S.P.A.; DE PIZZOL, Maria; SIRICO, Anna; ZIPPOLI, Mara; BIANCHINI, Gianluca; BECCARI, Andrea; ARAMINI, Andrea; LIBERATI, Chiara Rossana Maria; (53 pag.)WO2018/29150; (2018); A1;,
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Synthetic Route of 393-37-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparative Example P71 A/-(4-Bromo-2-(trifluoromethyl)phenyl)-2-methylpropane-2-sulfonamide (P71) To a solution of 2-methylpropane-2-sulfonamide (1.00 g, 7.30 mmol) in DMF (10 ml_) was added NaH (60% w/t in mineral oil, 350 mg, 8.80 mmol) at 0C and the solution was stirred for 30 min. Then a solution of 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (1.80 g, 7.30 mmol) in DMF (10 mL) was added and the solution was stirred at 120C overnight, cooled, diluted with H20 and extracted with EA (3x 20 mL). The combined organic phases were dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 8/1) to afford compound P71 (800 mg, 31%) as a colorless solid.

The synthetic route of 5-Bromo-2-fluorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2013/79223; (2013); A1;,
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Synthetic Route of 138526-69-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The amount ratio of the charged material is 3,4,5-trifluorobromobenzene: trimethyl borate = 1:1; Precipitating 28.476 g (0.14 mol) of 3,4,5-trifluorobromobenzene in 70 mL of tetrahydrofuran,Formulation to form a 3,4,5-trifluorobromobenzene solution.In a 1000 mL dry three-necked flask equipped with a thermometer and a constant pressure dropping funnel, 3.8 g of magnesium dust was added.(0.16mol),Tetrahydrofuran (30 mL), 1 mL of 1,2-dibromoethane and 5 mL of the above-prepared 3,4,5-trifluorobromobenzene solution were added dropwise under N2 protection.When the reaction is initiated at 5 to 10 C, a large amount of bubble temperature rises rapidly, and the solution slowly turns grayish black.And controlling the temperature to drop the remaining 3,4,5-trifluorobromobenzene solution (80 mL) of the above configuration at 10 C,The solution slowly turned black-gray, and after the addition was completed, it was kept at 25 C for 2 h.The reaction solution is then cooled to below -30 C (ie, the temperature at which the format reagent reacts with trimethyl borate),Adding a solution of trimethyl borate (dissolving trimethyl borate (14.56 g, 0.14 mol) in 50 mL of tetrahydrofuran to prepare a solution),And keep the temperature stable at -30 ~ -27 C, after the addition of trimethyl borate solution, continue the insulation reaction for 2h.Then, 135 mL of dilute hydrochloric acid having a concentration of 12% was added dropwise to the reaction solution, and the mixture was hydrolyzed at room temperature for 4 hours.After the completion of the hydrolysis reaction, ethyl acetate was added to the reaction mixture to extract a layer (50 mL × 3), and the extract phase was combined.The extract phase was dried over anhydrous sodium sulfate, and the solvent was evaporated to concentrate.Suction filtration to give a small amount of white solid washed with dichloromethane, and dried to give 10.8 g of white powder,That is, 3,4,5-trifluorobenzeneboronic acid represented by the formula (II) was obtained in a yield of 44%.

The synthetic route of 1-Bromo-3,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Li Zhenhua; Zhang Xuchao; Tan Zhiyong; (11 pag.)CN109761820; (2019); A;,
Bromide – Wikipedia,
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