Month: January 2021

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. Application In Synthesis of 5-Bromo-2-fluorobenzotrifluoride

A mixture of l-bromo-4-fluoro-3-(trifluoromethyl)benzene (5.02 g) and potassiumcyanide (1.38 g) in DMSO (20 ml) was heated at 80 C for 14 h. Water was added and themixture was extracted ether, the organic extracts were dried (MgSO4) and evaporated to givea brown oil. This was dissolved in DMSO (10 ml) and 4 M NaOH (10 ml) and heated at 100C for 16 h. 2 M Hcl (20 ml) was added and the mixture was extracted with DCM (threetimes), the organic extracts were dried (MgSO4), evaporated and purified by chromatography(silica, CH^Ck-MeOH-AcOH as eluent) to give the sub-title compound (1.99 g).MS: ESI (-ve): 268 [M-H]’ 100%.

The synthetic route of 393-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/21759; (2006); A1;,
Bromide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 546115-65-5, name is 1-(3-Bromophenyl)cyclopropanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 546115-65-5

To a solution of l-(4-fluoro-phenyl)-lH-pyrazolo[3,4-c]pyridine-4-carboxylic acid (0.500 g, 1.94 mmol), l-(3-bromophenyl)cyclopropanamine (453 mg, 2.14 mmol) and N,N-diisopropylethylamine (1.73 mL, 9.72 mmol) in DMF (18 mL) is added TBTU (0.780 g, 2.43 mmol). After 2 hours, the mixture is concentrated in vacuo, dissolved in ethyl acetate (200 mL), and washed with 2Nu sodium hydroxide (3 x 100 mL), saturated aqueous ammonium chloride (2 x 100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL). The organic layer is dried over MgS04, filtered through a pad of silica gel eluting with ethyl acetate (3 x 100 mL), and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 50-70% ethyl acetate in heptane to give a solid that is triturated with methylene chloride to afford the title compound as a solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 546115-65-5.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; MAO, Can; RAZAVI, Hossein; WO2011/49917; (2011); A1;,
Bromide – Wikipedia,
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These common heterocyclic compound, 6134-53-8, name is 4-Bromo-2,3-dihydro-1H-indene, 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. Quality Control of 4-Bromo-2,3-dihydro-1H-indene

A mixture of 4-bromoindane (60.0 mg, 304 umol), bis(pinacolato)diboron (92.7 mg, 365 umol), potassium acetate (59.7 mg, 608 umol) and Pd(dppf)Cl2 (11.1 mg, 15.2 umol) in dioxane (10 mL) was stirred at 90 C for 4 hrs under nitrogen. On completion, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate = 50:1) to give the title compound (50.0 mg, 57% yield) as a colorless oil.1H NMR (400MHz, CDCl3) delta = 7.60 (d, J = 7.2 Hz, 1H), 7.32 (d, J = 7.2 Hz, 1H), 7.14 (dd, J = 7.2, 7.2 Hz, 1H), 3.14 (t, J = 7.6 Hz, 2H), 2.90 (t, J = 7.6 Hz, 2H), 2.05 (m, 2H), 1.34 (s, 12H). (Intermediate C) 2-(1,3-Dihydroisobenzofuran-4-yl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane

The synthetic route of 4-Bromo-2,3-dihydro-1H-indene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 626-40-4, name is 3,5-Dibromoaniline, 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 626-40-4, category: bromides-buliding-blocks

3,5-Dichlorobenzoyl chloride (90.3 mg, 0.431 mmol) and 3,5-dibromoaniline (91.2 mg, 0.363 mmol) were stirred in THF (2.0 mL) for 1 h.The reaction was then diluted with H2O (~20 mL) and sonicated, and the resulting precipitate was filtered, rinsed with H2O, collected, sonicated with sat. NaHCO3(~10 mL), filtered, rinsed with H2O, and collected.Flash chromatographic purification over silica (4:1 hexanes:EtOAc) afforded 3,5-dichloro-N-(3,5-dibromophenyl)benzamide (217) as an off-white solid (125 mg, 81%).1H-NMR (500 MHz,d6-DMSO)d10.60 (s, 1H), 8.02 (d,J=1.7 Hz, 2H), 7.96 (d,J=1.9 Hz, 2H), 7.90 (t,J=1.9 Hz, 1H), 7.58 (t,J=1.7 Hz, 1H);13C-NMR (125 MHz, CDCl3)d163.02, 139.32, 136.93, 135.94, 132.22, 130.60, 125.69, 123.21, 121.82; ESI-TOF 421.8341m/z[MH]+, C13H8Br2Cl2NO requires 421.8344; RP-HPLC: 97% pure.

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Reference:
Article; Connelly, Stephen; Mortenson, David E.; Choi, Sungwook; Wilson, Ian A.; Powers, Evan T.; Kelly, Jeffery W.; Johnson, Steven M.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3441 – 3449;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3BrF4

Example 20 Synthesis of TRV 1 166[00146] TRV 1166 (4-(3-(isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l- yl)(phenyl)methanoneTRV 1166[00147] Scheme for TRV 1 166[00148] 4-bromo-2-fluorobenzotrifluoride (0.5181 g, 2.13 mmol), isopropyl amine (0.22 mL, 2.56 mmol), DIPEA (0.56 mL, 3.2 mmol) and NMP (3 mL) were added to a tube. The tube was sealed and heated overnight at 100 C. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HCI (2x), saturated NaHC03, H20 and brine before drying with Na2S0 . The material was filtered and concentrated under reduced pressure to give 0.1521 g of crude oil which was a 4:6 mixture of starting material to product, respectively. This material was dissolved in NMP (3 mL), treated with D PEA (0.07 mL, 0.38 mmol) and isopropyl amine (0.2 mL) and heated in a sealed tube at 115 C overnight. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give 0.1656 g of crude oil Purification of this material was not required. This aniline (0.1544 g, 0.55 mmol), benzoylpiperazine hydrochloride (0.1496 g, 0.66 mmol) and NaOiBu (0.1586 g, 1.65 mmol) were added to a tube. The tube was evacuated and flushed with argon for three cycles. Toluene (1.7 mL) and NMP (1.0 mL) were then added and the mixture was degassed with argon for 30 minutes. Pd2(dba)3 (0.0101 g, 0.01 1 mmol) and BetaGamma AlphaRho (0.0137 g, 0.022 mmol) were then added, the tube was sealed and heated overnight at 80 C. After cooling, the mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give a crude oil. Purification of this material via flash chromatography (20 % EtOAc / hexane) gave 0.125 g (58 % yield) of TRV 1166 (4-(3- (isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l-yl)(phenyl)methanone[00149] NMR (700 MHz, CDC13) delta = 7.46-7.41 (m, 5H), 7.30 (d, J = 8.4 Hz, 1 H), 6.21 (dd, J = 8.4, 2.1 Hz, 1H), 6.16 (s, 1H), 4.12-4.1 1 (m, 1H), 3.93 (br s, 2H), 3.68-3.66 (m, 1H), 3.59 (br s, 2H), 3.33 (br s, 2H), 3.18 (br s, 2H), 1.24 (d, J = 6.2 Hz, 6H).

According to the analysis of related databases, 142808-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, 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 67344-77-8, name: 1-(3-Bromophenyl)-N-methylmethanamine

Step 1: tert-Butyl 3-bromobenzyl(methyl)carbamate[00171] BOC20 (1.309 g, 1.378 mL, 5.998 mmol) was added to a stirred solution of l-(3- bromophenyl)-N-methyl-methanamine (1 g, 4.998 mmol) and Ets (606.9 mg, 836.0 mu^, 5.998 mmol) in DCM (20 mL) at ambient temperature and the reaction stirred for 16 hours. The reaction mixture was washed with 0.5M HC1 (x 1), water (x 2) and brine (x 1). The combined organic extractcs were dried (MgS04), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion.(TM)., 40 g column, eluting with 0 to 50percent EtO Ac/Petroleum Ether) to give the sub-title product as a colourless oil (1.44 g, 96percent Yield). XH NMR (400.0 MHz, DMSO) d 1.38 – 1.43 (2 x br s, 9H), 2.77 (s, 3H), 4.37 (s, 2H), 7.23 (d, 1H), 7.33 (t, 1H), 7.41 (s, 1H) and 7.48 (d, 1H) ppm; MS (ES+) 302.1.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus Alphonsus; PINDER, Joanne; YOUNG, Stephen, Clinton; REAPER, Philip, Michael; WO2011/143399; (2011); A1;,
Bromide – Wikipedia,
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Application of 126930-72-1, 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 126930-72-1 as follows.

A Schlenk tube was charged with Pd2dba3 (3.0 mg,0.32¡Á10-2 mmol, 8 mol%) and Xphos (3.1 mg, 0.65¡Á10-2 mmol, 16 mol%) in degassed toluene (2 mL). The reaction medium was heated under argon at 60 C for 10 min. To the violet solution was added, under a positive stream of argon, CLM1 (35 mg, 0.04 mmol, 1 eq.), 1-bromo-4-dodecylbenzene 2a (26 mg, 0.08 mmol, 2 eq.), and sodium-tert-butoxide(12 mg, 0.12 mmol, 3 eq.) in 2 mL of degassed toluene. The reaction mixture was heated at 95 C for 24 h. The solvent was evaporated under reduced pressure and the resulting mixture was extracted with DCM from a saturated aqueous solution of NaHCO3 (100 mL). The organic phase was washed with H2O (3¡Á100 mL), The desired product was purified by silica gel column chromatography with DCM/hexane (40:60 v/v) as eluent. Red solid (50 mg, 93%) 1H NMR (600 MHz, CD2Cl2, ppm): delta 7.56 (d, 4H, J=7.8 Hz, ArH), 7.12 (d, 8H, J=7.8 Hz,ArH), 7.03 (d, 12H, J=7.8 Hz, ArH), 2.95 (br, 12H, cyclohexyl-CH2,s),2.60 (t, 4H, J=7.8 Hz, CH2-(CH2)10CH3), 2.35 (s, 6H, CH3,s), 1.85 (br,12H, cyclohexyl-CH2,s), 1.65 (m, 4H, CH2-CH2(CH2)9CH3), 1.33 (m,36H, CH2-CH2(CH2)9CH3), 0.95-0.92 (m, 6H, CH2-CH2(CH2)9CH3); 13CNMR (150 MHz, CD2Cl2, ppm): delta 152.29, 148.39, 146.39, 146.29,137.39, 133.07, 132.63, 130.26, 129.57, 124.84, 124.55, 123.04,35.88, 32.53, 32.23, 30.28, 30.22, 30.13, 29.98, 29.96, 29.76, 26.78,23.29, 22.21, 21.06, 14.48. HR-MALDI-TOF; Calcd. for (M+)C80H104B2FeN8O6 1350.762; found 1350.525 UV-vis: (THF, 10-6 M),lambdamax [nm]=303, 448.

According to the analysis of related databases, 126930-72-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shetty, Suchetha; Baig, Noorullah; Al-Mousawi, Saleh; Al-Sagheer, Fakhreia; Alameddine, Bassam; Polymer; vol. 178; (2019);,
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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 138526-69-9

General procedure: 2-Amino-4-dimethylamino-6-phenyl-1,3,5-triazine (0.1076 g, 0.50 mmol) was added to the reaction vessel,P-methoxyiodobenzene (0.1170 g, 0.50 mmol), cuprous iodide (0.0285 g, 0.15 mmol), potassium carbonate(0.1380 g, 1.00 mmol), N, N’-dimethylethylenediamine (DMEDA, 0.0396 g, 0.45 mmol)Acetonitrile (3 mL) was added and the mixture was refluxed for 10 hours. After completion of the reaction, 4 mL of ammonia water was added and the mixture was stirred for 5 minutesSaturated aqueous NaCl (20 mL) was added and extracted with ethyl acetate (20 mL x 3). The organic layers were combined, concentrated,(Eluent: petroleum ether: ethyl acetate = 5: 1, v: v) and an Rf value of 0.4-0.45 (TLCThe eluent was separated and the solvent was removed by distillation under reduced pressure, and dried to obtain 0.1222 g of the aimed compound (IIII-1)Yield 76.0% The same operation as in Example 10 was repeated except that p-iodoanisole was replacedTrifluorobromobenzene (0.1057 g, 0.50 mmol),To give the title compound (IIII-17) (0.1218 g, yield 70.6%).

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; Zhejiang University of Technology; CUI, DONG MEI; LI, JIN JING; WU, KONG; ZHANG, CHEN; (15 pag.)CN105837525; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-52-5, 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. 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 1,4-dibromo-2-fluorobenzene (Combi-Blocks, 1000 g, 3938 mmol) in ethylene glycol (5100 mL), NMP (500 mL) was added at rt under nitrogen atmosphere. Then potassium tert-butoxide (1547 g, 1378 mmol) was added in portion over 45 min at 5 C and the resulting mixture was heated to 90 C for 16 h. Completion of the reaction was monitored by HPLC. The reaction mixture was cooled to rt and diluted with water (2000 mL) and stirred for 15 min at rt. The resultant solid was filtered and washed with ethylene glycol (300 mL x 2). To the filtrate, water (16000 mL) was added. The mixture was cooled to 10 C and stirred 1 h at the same temperature to get solid. The solid was filtered and washed with water (1000 mL x 2), pet ether (3 X 1000 mL) and dried. This solid was mixed with toluene and toluene was evaporated. This process was repeated 3 times (3 X 500 mL) to give the title compound. Yield: 78% (910 g, White solid). 1H NMR (400 MHz, CDCl3): delta 7.41 (d, J = 8.0 Hz, 1H), 7.06-7.00 (m, 2H), 4.14 (t, J = 4.0 Hz, 2H), 4.01 (q, J = 3.6 Hz, 2H). LCMS: (Method A) 296.0 (M+H), Rt. 3.97 min, 98.16% (Max). HPLC: (Method A) Rt. 3.67 min, 99.53% (Max), 99.38% (220nm).

The synthetic route of 1,4-Dibromo-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; KOEK, Johannes Nicolaas; (64 pag.)WO2017/144635; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 10269-01-9, 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 10269-01-9 as follows.

General procedure: Various amines (2.00mmol) were dissolved in absolute alcohol (15mL) and then potassium carbonate (2.00mmol) was added. The mixture was stirred for 45min at room temperature. Compound 4 (1.00mmol) and potassium iodide (0.25mmol) were added and the mixture stirred and refluxed overnight. Then the mixture was poured into water (50mL), extracted with ethyl acetate to give the crude product. The crude product was purified by column chromatography using petroleum ether and ethyl acetate. 6-Chloro-2-methoxy-N-(3-bromobenzyl)acridin-9-amine (LXL-4): Yield 69%; mp 156-159 C; 1H NMR (400 MHz, CDCl3): delta 8.08 (d, 1H, J = 1.8 Hz), 7.99 (d, 1H, J = 9.4 Hz), 7.91 (d, 1H, J = 9.3 Hz), 7.61 (s, 1H), 7.45 (d, 1H, J = 7.8 Hz), 7.39 (dd, 1H, J = 9.4, 2.6 Hz), 7.28 (dd, 2H, J = 6.6, 2.7 Hz), 7.22 (t, 1H, J = 7.7 Hz), 7.09 (d, 1H, J = 2.5 Hz), 4.76 (s, 2H), 3.76 (s, 3H); 13C NMR (101 MHz, CDCl3): delta 156.43, 149.09, 148.15, 146.93, 141.72, 134.92, 131.49, 130.99, 130.55, 130.38, 128.33, 125.88, 125.25, 124.99, 123.62, 123.13, 118.57, 116.52, 99.04, 55.39, 53.87; HR-MS(ESI): calcd. for C21H16BrClN2O [M+H]+ 427.0213; found: 427.0224.

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lang, Xu-Liang; Sun, Qin-Sheng; Chen, Yu-Zong; Li, Lu-Lu; Tan, Chun-Yan; Liu, Hong-Xia; Gao, Chun-Mei; Jiang, Yu-Yang; Chinese Chemical Letters; vol. 24; 8; (2013); p. 677 – 680;,
Bromide – Wikipedia,
bromide – Wiktionary