Tag: M.W=200-300

Synthetic Route of 418762-26-2,Some common heterocyclic compound, 418762-26-2, name is 4-Bromo-2-fluoro-5-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.

A suspension of 4-bromo-2-fluoro-5- methylaniline (15 g, 73.5 mmol) in 30 mL of concentrated HCl was added 30 mL of water and a solution of NaN02 (5.33 g, 77.2 mmol) in water (20 mL) was added over a 20 minute period at 0C. This diazonium solution was then brought to pH 6 with NaHC03. In a separate vial, a solution of CuS04 (22.9 g, 91.9 mmol) in water (100 mL) was added dropwise to a solution of KCN (23.9 mg, 368 mmol) in water (100 mL) at 0C, then toluene (100 mL) was added and the mixture was stirred and heated to 60C. The previously prepared diazonium solution was added dropwise to the brown CuCN solution at rt for 1 hour and EtOAc (100 ml) was added. The organic phase was washed with brine (200 mL) and concentrated. The crude product was purified via Prep-TLC to afford the 4-bromo-2-fluoro-5-methylbenzonitrile.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
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142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, belongs to bromides-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. Application In Synthesis of 4-Bromo-2-fluorobenzotrifluoride

Step 1: N- (3- (3-fluoro-4- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide and N- (3- (2-fluoro-3- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide[0359][0360]Toa solution of 4-bromo-2-fluoro-1- (trifluoromethyl) benzene (0.416 g, 1.7 mmol) in THF (3 mL) was added dropwise n-BuLi (2.5 M in hexane, 0.64 mL, 1.6 mmol) at -78 . The reaction solution was stirred for 1 hat -78 . To the reaction solution was added dropwise a solution of 2-methyl-N- (oxetan-3-ylidene) propane-2-sulfinamide (0.200 g, 1.1 mmol) in THF (7 mL) at -78 . The reaction solution was warmed slowly to room temperature and stirred for 16 h. The reaction solution was quenched with sat? d. aqueous NH4Cl (10 mL) . The mixture was extracted with EtOAc (3 x 30 mL) . The combined organic fractions was washed with brine (2 x 10 mL) , dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, usinggradient 0-70of ethyl acetatein petroleum ether as eluent. One isomer of the title compound N- (3- (3-fluoro-4- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide was obtained as a liquid.1HNMR (400 MHz, CDCl3) delta: 7.70-7.66 (m, 1H) , 7.37 (d, J 8.4 Hz, 1H) , 7.31 (d, J 11.2 Hz, 1H) , 5.10 (s, 2H) , 5.03 (d, J 7.2 Hz, 1H) , 4.87 (d, J 6.8 Hz, 1H) , 1.25 (s, 9H) . Another isomer of the title compound N- (3- (2-fluoro-3- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide was obtained as a liquid.1HNMR (400 MHz, CDCl3) delta: 7.54-7.49 (m, 3H) , 5.25-5.22 (m, 2H) , 4.88 (d, J 7.2 Hz, 1H) , 4.30 (d, J 6.8 Hz, 1H) , 1.25 (s, 9H) .

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FOSTER, Ashley; CHEN, Yili; DWYER, Michael; GUO, Zack Zhiqiang; WANG, Ming; XU, Shimin; BO, Yingjian; FU, Jianmin; (250 pag.)WO2017/277; (2017); A1;,
Bromide – Wikipedia,
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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. 626-40-4, name is 3,5-Dibromoaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Dibromoaniline

General procedure: In a nitrogen filled glove box, a 10 mL pressure tube, equippedwith a magnetic stir bar was loaded with the titanium catalyst(0.10 mmol) and dissolved in dry toluene (2 mL). The solutionwas loaded with the aniline derivative (1.0 mmol), alkyne derivative(1.0 mmol) and tert-butylisonitrile (1.5 mmol). The pressuretube was sealed with a Teflon screw cap, taken out of the dry boxand heated at 100 C for 24-48 h in a silicone oil bath. Volatileswere removed in vacuo, and glacial acetic acid (2 mL) was added.The mixture was then heated at 150 C for 24 h. The pressure tubewas then allowed to cool to room temperature, diluted in dichloromethaneand neutralized with saturated NaHCO3 solution. Theorganic layer was further extracted with additional dichloromethane,washed with brine, dried over NaSO4, filtered and concentratedin vacuo. The crude product was dry loaded onto aluminaand purification was accomplished by column chromatography on neutral alumina using hexanes/ethyl acetate (9:1, v/v) as the eluentto provide the desired quinoline.4.1.1. 5,7-Dimethyl-3-phenylquinoline (4)Pale yellow solid 128 mg (55%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; McDaniel, Tanner J.; Lansdell, Theresa A.; Dissanayake, Amila A.; Azevedo, Lauren M.; Claes, Jacob; Odom, Aaron L.; Tepe, Jetze J.; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2441 – 2450;,
Bromide – Wikipedia,
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These common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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. category: bromides-buliding-blocks

3.6-Dihydro-2H-pyran-4-boronic acid pinacol ester (5.62 g, 26.75 mmol), 4-bromo-3-fluorobenzotrifluoride (5.00 g, 20.58 mmol), potassium carbonate (8.53 g, 61.73 mmol) and 1,1?-bis(diphenylphosphino)ferrocenedichloro palladium(II) (753 mg, 1.03 mmol) were suspended in 50 mL of 1,4-dioxane and 10 mL of water. The reaction mixture was refluxed for 3 hrs, solvents were evaporated and the crude was extracted with ethyl acetate (50 mL) and water (50 mL). Organic layer was separated, dried over sodium sulfate and evaporated. The crude obtained was purified by flash chromatography (eluent: cyclohexane/AcOEt; gradient from 40% to 100% of AcOEt) to obtain 4.0 g of the title compound as clear oil.GC-MS (Method 9): Rt=7.76 minMS: m/z=246 (M)+

The synthetic route of 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; HOENKE, Christoph; BERTANI, Barbara; FERRARA, Marco; FOSSATI, Giacomo; FRATTINI, Sara; GIOVANNINI, Riccardo; HOBSON, Scott; (88 pag.)US2017/101411; (2017); A1;,
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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. 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrF4

(1) To a solution of Compound 1 (1 g) and Compound 2 (870 mg) in toluene (2.5 mL) was added a solution of potassium bis(trimethylsilyl)amide in toluene (0.5 mol/L, 8.23 mL) under nitrogen atmosphere at room temperature, and then the mixture was heated under reflux for 15 minutes. To the reaction mixture was poured a saturated aqueous solution of ammonium chloride under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of hydrochloric acid (1 mol/L), a saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, dried, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=90:10-80:20) to give Compound 3 (1.08 g) as a pale yellow viscous material. MS (APCI): m/z 333/335 [M-Boc+H]+

The synthetic route of 68322-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; YAMAMOTO, Yasuo; SATO, Atsushi; MOROKUMA, Kenji; SHITAMA, Hiroaki; ADACHI, Takashi; MIYASHIRO, Masahiko; (260 pag.)EP3150578; (2017); A1;,
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Synthetic Route of 1435-51-4, 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,3-Dibromo-5-fluoro-benzene (20 g, 78.77 mmol, 1 eq) was dissolved in i-Pr2O (200 mL) in a dried flask under nitrogen. The reaction mixture was cooled to -78 C and stirred under nitrogen atmosphere. n-BuLi (2.5 M, 31.5 mL, 1 eq) was added drop wise to the above solution and the reaction mixture was stirred at -78 C for 30 min. After complete addition of n-BuLi, N-methoxy-N-methyl-acetamide (9.75 g, 94.5 mmol, 10.05 mL, 1.2 eq) dropped to the above reaction mixture, while keeping the reaction mixture below -78 C. After addition, the reaction mixture was warmed slowly to 30 C for 30 min. The reaction mixture was poured into water (150 mL) and the reaction mixture was stirred for 15 min. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (150 mL), combined organic phase, dried over anhydrous Na2SO4, filtered and evaporated in vacuum to give residue (16 g crude). The residue was purified by flash silica gel chromatography (ISCO; 120 g CombiFlash Silica Flash Column, Eluent of 0~10% Ethyl acetate/Petroleum ether gradient 85 mL/min). Compound was obtained as off-white solid (11.3 g, yield 66%).1H NMR (400 MHz, CDCl3) delta ppm 7.91 – 7.84 (m, 1H), 7.63 – 7.54 (m, 1H), 7.45 (td, J=2.0, 7.8 Hz, 1H), 2.63 – 2.55 (m, 3H).

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

Reference:
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
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Related Products of 51554-93-9, The chemical industry reduces the impact on the environment during synthesis 51554-93-9, name is 1-Bromo-4-octylbenzene, I believe this compound will play a more active role in future production and life.

According to the following scheme, in an atmosphere of nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (2.3 g) and 2N aqueous sodium carbonate solution (10 ml) are added to a mixed solution of 1-bromo-4-n-octyl benzene (25.0 g), 2-thiopheneboronic acid (10.8 g) and tetrahydrofuran (THF) (100 ml), and the mixture is refluxed for 10 hours. After the reaction is finished, the mixture is subjected to extraction with toluene, and the resultant organic phase is sufficiently washed with pure water. Subsequently, after the organic phase is dried with anhydrous sodium sulfate, the solvent is distilled away under reduced pressure, and the resultant product is subjected to a silica gel column chromatographic process (eluent: hexane) to separate the aimed product, thereby obtaining 26.2 g of Intermediate 1.

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-4-octylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJI XEROX CO., LTD.; US2010/197942; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromodibenzo[b,d]furan

15.5 g (72 mmol) of the intermediate (13) obtained in [Reaction Formula 16] and 16.2 g (65.5 mmol)1-bromodibenzofuranyl group, added to a 1 L three-necked flask,Add 300 ml of toluene and 75 ml of ethanol to dissolve, and pass nitrogen for 15 minutes.An additional 98.3 ml of an aqueous solution of K2CO3 (196.5 mmol, 2 M) was added.Finally, 1.5 g of Pd(PPh3)4 (2 molpercent) was added. Warming up to 110 ° C,The reaction was completed in 12 hours. Adsorption with activated carbon, suction filtration, solvent removal, drying, recrystallization from toluene and ethanol afforded 19 g of intermediate (14), yield 86percent.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Bu Gonggaofamingren; (47 pag.)CN108148037; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 3972-64-3, 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 1.6M solution of”butyllithium (0.85 mL, 1. 36 mmol) was added to a solution of dicyclohexylamine (0. 27 mL, 1.36 mmol) in toluene (5 mL). After stirring for 5 min, a mixture of cisltrans isomers of 2-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester (269 mg, 1.11 mmol) was added. After stirring for 30 min, 1-bromo-3-ferf-butyl-benzene (248 mg, 1.16 mmo 1) was added followed by the simultaneous addition of tri-tert-butylphosphonium tetrafluoroborate (31 mg, 107 umol) and tris (dibenzylideneacetone) dipalladium (0)-chloroform adduct (51 mg, 49.3 umol). The solution was placed into a preheated oil bath at 60 C. After stirring for 20 h, the solution was diluted with 10percent aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49: 1,24 : 1, and 23: 2 hexanes: ethyl acetate as the eluant to yield 375 mg (90percent yield) of a mixture of cisltrans isomers of 1-(3-feff-butyl-phenyl)-2-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow oil. Method [2] Retention time 3.67 min by HPLC and 3.75 min by MS (M+Na=397). Method [2] Retention time 3.77 min by HPLC and 3.85 min by MS (M+Na=397).

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87752; (2005); A2;,
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Reference of 103273-01-4,Some common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

2 – Bromo -4 -tert-butylaniline (2 – Bromo – 4 – tertbutylaniline) 40.0g (175.34 mmol), 4 – bromobenzoyl chloride (4 – Bromobenzoyl chloride) 38.4g (175.34 mmol) and THF 360 ml 3 hoursAfter completion of the reaction, the solvent was distilled under reduced pressure. A yellowish solid compound (intermediate (7)) 55.8g (=unitz ) was obtained by solid formation using diisopropyl ether (IPE) to give a solid compound having a yellowish 77.4% color.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Co., Ltd. Leputuo; Wu Weizhen; Han Jiazhong; Jin Huizhen; Jin Xiane; Jin Kuili; Ren Zhezhu; Xi Wenji; Gao Bingzhu; (46 pag.)CN109988119; (2019); A;,
Bromide – Wikipedia,
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