Tag: M.W=200-300

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. 4263-52-9, name is Sodium 2-bromoethanesulphonate, This compound has unique chemical properties. The synthetic route is as follows., 4263-52-9

A mixture of sodium-2-bromoethanesulfonate (41 1 mg, 1.95 mmol), N-methyltetradecylamine (342 mg, 1.50 mmol), K2C03 (269 mg, 1.95 mmol) and DMF (3 mL) is stirred at 135C bath temperature under argon atmosphere overnight. The volatiies are removed on a rotary evaporator and the residue purified by preparative HPLC to yield 324 mg (64%) of 1 s.1H-NMR (300 MHz, CDCI3): delta = 0.90 (t, J = 6.4, 3H), 1.15-1.45 (m, 22H), 1.78 (m, 2H), 2.97 /2.99 (2s,? = 3H), 3.05-3.55 (m, 5H), 3.64 (m, 1 H), 7.36 (br. s, 1 H).MS (ESI): 336.3 (M+H+), 671.5 (2M+H+), 693.5 (2M+Na+), 709.5 (2M+K+).

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; JADO TECHNOLOGIES GMBH; TECHNISCHE UNIVERSITAeT DRESDEN; SCHLECHTINGEN, Georg; KNOeLKER, Hans-Joachim; FRIEDRICHSON, Tim; JENNINGS, Gary; BRAXMEIER, Tobias; WO2012/160187; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 73918-56-6 as follows. 73918-56-6

To a suspension of 2-(4-bromophenyl)ethan-1-amine (1) (3.1?mL, 20?mmol) in CH2Cl2 (30?mL) was added dropwise (Boc)2O (5.97?mL, 26?mmol) at 25?C and the solution was stirred for 4?h. After the reaction completed, the solvent was removed under reduced pressure. The residue was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50?mL?*?3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was purified by column chromatography to give tert-butyl(4-bromophenethyl)-carbamate (2) (5.0?g, 84% yield) as a white solid. 1H NMR (400?MHz, CDCl3) delta: 7.42 (d, J?=?8.2?Hz, 2H), 7.07 (d, J?=?8.1?Hz, 2H), 4.52 (s, 1H), 3.35 (s, 2H), 2.75 (t, J?=?6.9?Hz, 2H), 1.43 (s, 9H).

According to the analysis of related databases, 73918-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Wenhua; Huang, Zhenghui; Wang, Wanyan; Mao, Fei; Guan, Longfei; Tang, Yun; Jiang, Hualiang; Li, Jian; Huang, Jin; Jiang, Lubin; Zhu, Jin; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6467 – 6478;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, molecular formula is C6H4BrF2N, 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. 203302-95-8.

A mixture of 4-bromo-3,5-difluoro-phenylamine (6.0 g, 28.8 mmol), ferrous sulfate (1.82 g), glycerol (8.6 mL), nitrobenzene (1.79 mL) and 5.0 ml of concentrated sulfuric acid (5 mL) was heated gently. After the first vigorous reaction, the mixture was heated to reflux for five hours. Nitrobenzene was removed by distillation in vacuo. The aqueous solution was acidified with glacial acetic acid, and dark brown precipitate separated, which was purified by flash chromatography (silica gel, petroleum:ethyl acetate= 12:1) to return title compound as a white solid (3.5 g, 49.8%).

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

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2008/144767; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

142808-15-9, Name is 4-Bromo-2-fluorobenzotrifluoride, 142808-15-9, 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.

a) 6-[3-Fluoro-4-(trifluoromethyl)phenyl]-8-nitro-3,4-dihydro-2(1 H)-quinolinoneTo a stirred solution of 4-bromo-2-fluoro-1-(trifluoromethyl)benzene (1.0 g, 4.1 mmol), bis(pinacolato)diboron (1.1 g, 4.3 mmol) and potassium acetate (1.2 g, 122 mmol) in dimethylformamide (50 mL) was added [1 ,1′- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (81 mg, 0.11 mmol). After purging with nitrogen, the reaction was heated to 80 0C and EPO stirred for 2 h. 6-bromo-8-nitro-3,4-dihydro-2(1 H)-quinolinone (example 77a, 1.0 g, 3.7 mmol), cesium fluoride (1.3 g, 8.4 mmol), and tetrakis(triphenylphosphine)palladium (0) (130 mg, 0.11 mmol) were added and the reaction stirred at 100 0C for 18 h. After cooling to room temperature, the reaction was evaporated to dryness under vacuum. The residue was taken up in ethyl acetate, filtered to remove insolubles, washed with 1 M aq hydrochloric acid, brine, dried (MgSO4), filtered and concentrated under vacuum. Purification by flash chromatography on silica gel (3% ethyl acetate/dichloromethane) gave the title compound (0.77 g, 59%) as a yellow solid. MS (ES) m/e 355.0 (M + H)+.; +/- 6-f3-Fluoro-4-(trifluoromethvnphenyl1-3-hyclroxy-3.4-dihvdro-2(1 H)-quinolinone 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (0.091 mL, 0.375 mmol), bis(pinacolato)diboror) (0.10 g, 0.394 mmol), potassium acetate (0.11 g, 1.12 mmol), dichloro[1 ,1 ‘-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.020 g, 0.027 mmol) in DMF (2.0 mL) were heated to 800C under nitrogen for 2.5 hours. After the reaction was cooled, dichloro[1 ,1’- bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.020 g, 0.027 mmol) was added followed by addition of + 6-bromo-3-hydroxy-3,4-dihydro- 2(1 H)-quinolinone (example 85b, 0.095 g, 0.392 mmol) and 2M Na2CO3 in water (0.98 mL). The reaction was heated to 800C. After 12 hours the reaction mixture was cooled and diluted with ethyl acetate, then washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified using reverse-phase preparative HPLC (10% CH3CN/H2O to 100% CH3CN/H2O with 0.1% TFA) to give the title compound as a solid. 1H NMR (400MHz, D6-DMSO) delta 10.34 (bs, 1 H), 7.79 (m, 2H), 7.69 (m, 2H), 7.59 (d, J = 8.6Hz, 1 H), 6.96 (d, J = 8.3 Hz, 1 H), 5.58 (bs, 1 H), 4.18 (m, 1 H), 3.13 (dd, 1 H), 2.93 (dd, 1 H).

Statistics shows that 4-Bromo-2-fluorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 142808-15-9.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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. 24358-62-1

7-Fluoro-lH-benzo[d][l,3]oxazine-2,4-dione (0.500 g; 2.76 mmol), l-(4- bromophenyl)ethanamine (0.474 ml; 3.31 mmol), urea (0.249 g; 4.14 mmol), and 3 ml of DMA were charged in a microwave tube and heated for 10 min at 250 C. The reaction mixture was cooled to rt, mixed with water, and extracted twice with EtOAc. Combined organic phases were dried over Na2S04 and evaporated to dryness. The crude product was purified with CombiFlash (normal phase silica) to yield 389 mg of 3-(l-(4- bromophenyl)ethyl)-7-fluoroquinazoline-2,4(lH,3H)-dione. 1H-NMR (400 MHz, d6- DMSO): delta 1.77 (d, 3H), 6.11 (q, 1H), 6.22 (d, 1H), 6.60 (dd, 1Eta),7.19-7.26 (m, 2H), 7.45- 7.50 (m, 2H), 7.66 (d, 1H), 10.96 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24358-62-1, its application will become more common.

Reference:
Patent; ORION CORPORATION; PRUSIS, Peteris; HOeGLUND, Lisa; TOeRMAKANGAS, Olli; HIETANEN, Ari; ARVELA, Riina; VESALAINEN, Anniina; HEIKKINEN, Terhi; WO2015/169999; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, 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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 14; ralphac-(35r,4i?)-7V-cyclopropyl-4- [2-fluoro-4-(trifluoromethyl)phenyl] -4-hydroxy-iV- [3 -(2- methoxyethoxy)-5 -(3 -methoxypropyl)benzyl]piperidine-3 -carboxamide; Step 1: rac-tert-butv (3?4i?V3-alphacvclopropyir3-q-methoxyethoxy)-5-(3- methoxypropyDbenzyll amino } carbonyl)-4- [2-fluoro-4-(trifluoromethyl)phenyl] -4- hydroxypiperidine- 1 -carboxylate; ?-BuLi (2.50 M in THF, 3.11 eq.) was added to a stirred solution of l-bromo-2- fluoro-4-(trifluoromethyl)benzene (3.24 eq.) in THF (1.6 M) at -78 C. The mixture was stirred at -78 0C for 15 min then MgBr2-Et2O (0.4 M in THF, 3.32 eq.) was added dropwise. The mixture was stirred -78 C for 30 min. The resulting solution was cannulated into a solution of keto amide 3.1 (1 eq.) in THF (0.15 M) at -78 C. The reaction mixture was stirred at -78 C for 1 hr then allow to warm slowly to rt with stirring over 12 h. The mixture was quenched with saturated NH4Cl, diluted with Et2O. The organic extract was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (10-75% EtOAc in hexanes) to give the title compound as an oil.

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; MERCK FROSST CANADA LTD.; WO2009/70869; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 7617-93-8, name is 2-Bromo-1,4-bis(trifluoromethyl)benzene, molecular formula is C8H3BrF6, 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. 7617-93-8

All experiments were performed in a previously-described quadrupole ion trap mass spectrometer (modified ThermoFinnigan LCQ DECA) equipped with electrospray ionization (ESI) [15, 17]. In a typical experiment, the dianion precursor was dissolved in methanol (10-4 M) and injected through the electrospray interface at flow rates ranging from 3 to 5 muL/min. The neutral reagents were mixed into the buffer gas by injecting a constant flow of reagent (20-400 muL/h) into a measured flow of helium (1000-1500 mL/min). Reactions were monitored as a function of time at various flow rates (pressures) of the reagent and branching ratios were determined. Time delays and reagent flows were adjusted to obtain plots that covered two to three half-lives of the reactant ion. Reported rate constants were measured at three different reagent flow rates and at least nine kinetic runs were collected on 2 or more days (>18 runs). In the past, we have shown that the ion trap gives reactivity at near ambient temperature [18]. All the arene reagents were obtained from commercial sources.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7617-93-8, its application will become more common.

Reference:
Article; Eanes, Allison D.; Noin, Diogo O.; Kebede, Maheteme K.; Gronert, Scott; Journal of the American Society for Mass Spectrometry; vol. 25; 1; (2014); p. 10 – 17;,
Bromide – Wikipedia,
bromide – Wiktionary

327-52-6, A common compound: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

[0122] Into a 100 mL three- necked flask were added 4.62 g 1- bromo- 2, 4, 5- trifluorobenzene (0.022 mol) andanhydrous tetrahydrofuran (50 mL) . The resulting mixture was cooled to- 20 C. The solution of isopropylmagnesiumbromide (22 mmol) in tetrahydrofuran (22 ml, 1 M THF) was slowly added dropwise under nitrogen. After the additionwas complete, the reactants were maintained at- 20 C for later use.[0123] Cuprous bromide – dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. Theresulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise undernitrogen. After 15 min, a solution of the acridine compound as shown in the above reaction formula (4.16 g, 0.015 mol)in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammoniachloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separatedwater layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together andfurther was washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followedby filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtaina compound (4.98 g, 0.0128 mol, yield 85%).1H NMR (400 MHz, CDCl3) delta 7.87?7.61 (m, 5H), 7.15?6.94 (m, 1H), 6.88 (d, J = 6.8 Hz, 1 H), 5.02 (d, J = 8.9 Hz, 1 H),4.00 – 3.80 (m, 1 H), 2.92?2.76 (m, 1 H), 2.76?2.64 (m, 1H), 2.64? 2.44 (m, 2H), 2.06 (d, J = 14.6 Hz, 3H), 1.84 (s, 1H), 1.62 (s, 1H). Ms (M++1): 390.

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-2,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Hisoar Pharmaceutical Co., Ltd; PAN, Xianhua; LI, Weijin; ZHANG, Qunhui; RUAN, Libo; YU, Wansheng; DENG, Fei; MA, Tianhua; HUANG, Mingwang; HE, Minhuan; EP2647624; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

699-03-6, A common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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 solution of 4-bromo-N-methylbenzylamine (199 mg,1.00 mmol), 3-pyridylboroxine (163 mg, 0.518 mmol), sodium carbonate (2 M, 4mL) and tetrakis(triphenylphosphine)-palladium(0) (30 mg, 0.026 mmol) in 1,4-dioxane (50 mL) was refluxed for 18 h. The solvent was eliminated under reduced pressure and the crude material was dissolved in a mixture of CH2Cl2 and CH3OH (1:1, 10 mL) and filtered through celite. After evaporation of the solvent, the crude material was purified by flash column chromatography (hexanes: ethyl acetate 6:4 and 1 % NEt3) to afford 1 as yellow oil (165 mg, 83 %); 1HNMR (CD2Cl2, 500 MHz): delta = 8.83 ppm (dd, J = 2.4 and 0.7 Hz, 1H), 8.54 (dd, J = 4.8 and 1.6 Hz, 1H), 7.89 (ddd, J = 7.9, 2.3 and 1.7 Hz, 1H), 7.58-7.56(m, 2H), 7.45-7.43 (m, 2H), 7.35 (ddd, J= 7.9, 4.8 Hz and 0.8 Hz, 1H), 3.78 (s, 2H), 2.43 (s, 3H), 1.64 (s, 1H); 13CNMR (125 MHz, CD2Cl2): delta = 148.9 ppm, 148.8 141.2, 137.0,136.9, 134.6, 129.4, 127.5, 124.1, 56.1, 36.3; IR (NaCl): nu = 3300 cm-1, 3028, 2933, 2844,2790, 2360, 1918, 1684, 1653, 1577, 1559, 1517, 1474, 1429, 1396, 1354, 1188,1129, 1103, 1024, 1001, 848, 796, 711; MS (CI, CH5+): m/z (%) = 199 (100) [M+H]+,168 (20), MS (EI, 70 eV): m/z (%):198 (100) [M]+, 168 (66), 156 (40); HR-MS (EI, 70 eV): m/z =198.11338 [M]+: calcd for C13H14N2:198.11570.

The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keller, Marco; Wolfgardt, Annette; Mueller, Christoph; Wilcken, Rainer; Boeckler, Frank M.; Oliaro-Bosso, Simonetta; Ferrante, Terenzio; Balliano, Gianni; Bracher, Franz; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 13 – 22;,
Bromide – Wikipedia,
bromide – Wiktionary

1559-88-2, 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 1559-88-2 as follows.

A solution of 1-bromo- 2,3,5,6-tetrafluorobenzene (4.58 g, 20 mmol) in 100 mL of anhydrous THF was cooled to -100 C (liquid nitrogen/ EtOH) under nitrogen. Then 1.4M solution of sec-BuLi in cyclohexane (15 mL, 21 mmol) was added dropwise at -100 C to -90 C. The mixture was stirred at -100 C to -90 C for 10 min, then a solution of R-(+)-propylene oxide (1.51 g, 1.8 mL, 26 mmol) in 15 mL of THF was added dropwise at -100 C to -90 C, then the mixture was cooled to -105 C and a 46.5% solution Of BF3 in diethyl ether (4.18 mL, 30 mmol) was added dropwise. The mixture was stirred at -100 C to -90 C for 2 h, then the reaction was quenched with 20 mL of sat. aq. NH4Cl at -90 C. The mixture was stirred and warmed to 0 C overnight. Then 20 mL of water was added and mixture was extracted with EtOAc (2×60 mL), the extract was dried over Na2SO4 and evaporated to give crude oil, which was purified by column (silicagel, EtOAc/hexane 1 :9, Rf = 0.57 in EtOAc/hexane 3:7) to give (2R)-1-(2,3,5,6-tetrafluorophenyl)propan-2- ol (2.57 g, 62 %) as a white solid. 1H NMR (300 MHz, CDCl3): delta 6.96 (m, 1H), 4.1 1 (m, 1H), 2.89 (m, 2H), 1.47 (d, J = 5.46 Hz, 1H), 1.29 (d, J = 6.21 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1559-88-2, and friends who are interested can also refer to it.

Reference:
Patent; CHEMBRIDGE CORPORATION; WO2009/117097; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary