Month: July 2021

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 7617-93-8 as follows. HPLC of Formula: C8H3BrF6

2,5-BIS (TRIFLUOROMETHYL) BROMOBENZENE (0.59 G, 2.00 MMOL, 1.00 EQUIV. ), 4- nitrophenylbronic acid (0.334 g, 2. 00 mmol, 1.00 equiv. ), trans- benzyl (chloro) bis (TRIPHENYLPHOSPHINE) PALLADIUM (LL) (0.076 g, 0.10 mmol, 0.05 EQUIV.), K2CO3 1.38 g, 10.00 MMOL, 5.00 equiv. ) and 10 mL dry NMP were charged to a 25 mL round bottom flask. The mixture was thoroughly de- oxygenated by subjecting to vacuum/nitrogen cycle three times, and heated at 110 C for 2 days under nitrogen protection. Usual workup yielded crude product 4′-nitro-2, 5-bis-trifluoromethyl-biphenyl as brown viscous oil (0. 66 g, 1.97 mmol, 99%). H NMR (300 MHz, CDCl3), 6 (ppm): 8.32 (d, J = 8.7 Hz, 2H); 7. 82-8. 00 (m, 2H); 7.52-7. 61 (m, 3H).The crude product made in the last step was dissolved in 10 mL methylene chloride and 10 mL ethanol. Tin (II) CHLORIDE (2.28 g, 12.00 mmol, 6.00 equiv) was added, followed by addition of 1 mL water. After stirring at room temperature for 2 days, the mixture was neutralized with 2 N NAOH solution, and subjected to usual workup to yield crude product 4′-amino-2, 5-bis-trifluoromethyl- biphenyl (0.52 g, 1.70 mmol, 85% crude yield) as brown viscous oil.4′-Amino-2, 5-bis-trifluoromethyl-biphenyl (0.16 g, 0.50 mmol, 1.00 equiv) was dissolved in 10 mL methylene chloride. To the solution was added 2,3- DIFLUOROBENZOYL chloride (0. 088 g, 0.50 mmol, 1.00 equiv), and triethylamine (0.061 g, 0.60 mmol, 1.20 equiv). The mixture was stirred at room temperature for one hour, and loaded to column for flash chromatography. The title compound was isolated as light yellow solid (0.12 g, 0.27 mmol, 54%). 1H NMR (300 MHz, CDCI3), 6 (PPM) : 8. 39 (D, J= 10.5 Hz, 1H) ; 7.75-7. 95 (m, 6H); 7.63 (s, 1H); 7.26-7. 443 (m, 3H); ESMS CALCD. FOR C21H12F8NO (M + H) + : 446.0 ; Found: 446.0

According to the analysis of related databases, 7617-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS, CORP.; WO2005/9954; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 76153-06-5, These common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, 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.

EXAMPLE 375-Methyl-7-r3-(piperidin-l-ylmethyl)phenyl]quinoxalineGlyoxal (10 drops of a 40% solution in water) was added to a solution of 5- bromo-2,3-diaminomethylbenzene (80 mg, 0.4 mmol) in ethanol (3 mL). The mixture was stirred and left to stand at r.t. for 1 h. The mixture was partitioned between water and EtOAc (20 mL each), and the organic phase was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DME (1.2 mL), and 3-(piperidin-l-ylmethyl)phenyl- boronic acid pinacol ester hydrochloride (135 mg, 0.4 mmol), 2M aqueous sodium carbonate solution (0.6 mL, 0.9 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) were added. The mixture was heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. The mixture was partitioned between water and EtOAc (2 mL each), and the organic phase was concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (5 mg, 4% over the two steps) as a pale yellow-brown gum. delta? (CDCl3) 8.87 (d, IH), 8.85 (d, IH), 8.17 (s, IH), 7.93 (s, IH), 7.72 (s, IH), 7.65 (d, IH), 7.46 (t, IH), 7.39 (d, IH), 3.58 (s, 2H), 2.88 (s, 3H), 2.34-2.52 (m, 4H), 1.51-1.68 (m, 4H), 1.39-1.51 (m, 2H). LCMS (ES+) 318 (M+H)+, RT 2.43 minutes.

Statistics shows that 5-Bromo-3-methylbenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 76153-06-5.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1435-51-4,Some common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

Sodium methoxide (4.5M solution in methanol, 8.80 [ML,] 41.0 [MMOL)] was added dropwise to a stirred solution of 3, 5-dibromofluorobenzene (5.00 g, 19.0 [MMOL)] in [N, N-DIMETHYLFORMAMIDE] (95 ml) at [0C] under a nitrogen atmosphere. The reaction was warmed to room temperature, stirred for 1 hour and then evaporated under reduced pressure. The residue was dissolved in diethyl ether and was washed with water [(3X300] [ML)] and brine (300 [ML),] dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound as a white solid (5.13 g). ‘H-NMR [(300MHZ,] CDC13) : [8] 3.79 (s, 3H), 7.00 (s, 2H), 7.26 (s, [1 H).] LRMS: m/z TS+ 266 [[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 1,3-Dibromo-5-fluorobenzene, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 452-63-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 452-63-1 name is 1-Bromo-4-fluoro-2-methylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of bis (dibenzylidene acetone) palladium (0) (0.719 g, 1.25 mmol) and tris (2-methylphenyl) phosphine (0. 761 g, 2. 50 mmol) in toluene (150 mL) were added sodium tert- butoxide (3. 36 g, 35.0 mmol), 2-BROMO-5-FLUOROTOLUENE (3.16 mL, 25.0 mmol) and tert-butyl 1-piperazinecarboxylate (5.03 g, 27.0 mmol) at room temperature, and the mixture was stirred under a nitrogen atmosphere at 100C for 20 hrs. After cooling, the reaction mixture was washed with water and saturated brine, dried (MGS04) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 9/1) to give the title compound as a yellow oil (2.50 g, yield 34%). 1H NMR (300 MHz, CDC13) 8 PPM : 1.49 (s, 9 H), 2.30 (s, 3 H), 2.77-2. 80 (m, 4 H), 3.54-3. 57 (m, 4 H), 6.80-6. 96 (m, 3 H). LC/MS (ESI) m/z 295 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2004/46107; (2004); 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. 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 202865-83-6

A solution of 1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), 1-bromo-3- fluoro-5-methylbenzene (23 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2CO3 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H2O (4:1, 2.1 mL) was heated at 85 C for 18 hours. LiOH (12.4 mg, 0.52 mmol) was added and the reaction was heated at 90 oC under microwave radiation for 45 minutes.1 N HCl (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep HPLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of NH4CO2H) (60 to 80%). The product was lyophylised and afforded the title compound (13 mg, 0.024 mmol, 24%) as a pale yellow solid. [389] 1H NMR (500 MHz, DMSO) delta 8.21 (d, J = 2.0 Hz, 1H), 8.02 (dd, J = 8.5, 2.0 Hz, 1H), 7.75 (d, J = 8.5 Hz, 1H), 7.13 (s, 1H), 7.11 (d, J = 9.9 Hz, 1H), 7.07 (d, J = 9.7 Hz, 1H), 3.35 (hept, J = 6.7 Hz, 1H), 2.36 (s, 3H), 2.31 (s, 3H), 1.24 (d, J = 6.7 Hz, 6H); MS (m/z): 536.0 [M+H]+.

The synthetic route of 202865-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M., Arshad; CIBLAT, Stephane; DERY, Martin; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu; SRIVASTAVA, Sanjay; SHIPPS, Gerald, W.; COOPER, Alan, B.; BRUNEAU-LATOUR, Nicolas; LY, Vu, Linh; (314 pag.)WO2016/196644; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1647-26-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1647-26-3 name is 1-Bromo-2-cyclohexylethane, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(a) 2-(8-Cyclohexyloctyl)-benzaldehyde To an ice cold solution of 1-hexyne (49.6 mmoles) in freshly distilled tetrahydrofuran (50 ml) containing a trace of triphenylmethane was added dropwise n-butyl lithium in hexane (49.5 mmoles). About 10 minutes after the addition was stopped, sieve dried hexamethylphosphoramide (57.5 mmoles) was added and the solution stirred for 10 minutes. A solution of 2-cyclohexylethyl bromide (51.3 mmoles) in tetrahydrofuran (10 ml) was added and the reaction mixture was stirred for about 3 hours as the temperature rose to room temperature. The mixture was taken up in ether (100 ml) and washed with water (3*100 ml) and sodium chloride solution (100 ml). The organic phase was dried over magnesium sulfate and evaporated to leave an oil which was purified by flash chromatography to give 1-cyclohexyloct-3-yne.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-cyclohexylethane, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline Beckman Corporation; US4730005; (1988); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 6274-57-3,Some common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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) 4-(4-Dimethylaminomethylphenyl)-4-hydroxycyclohexanone-ethylene ketal To a solution of 36.4 g (0.17 mol) of 4-bromo-N,N-dimethylbenzylamine in 250 ml of dry tetrahydrofuran, cooled to -70 C., are added dropwise, under a nitrogen atmosphere and with stirring, 112 ml (0.179 mol) of a 1.6 molar solution of n-butyllithium in hexane in such a way that the temperature does not exceed -65 C. The orange solution is stirred for a further 15 minutes at -70 C. and then within 10 minutes a solution of 27.6 g (0.172 mol) of 1,4-cyclohexanedione-monoethylene ketal in 110 ml of tetrahydrofuran is added, whilst the temperature must not exceed -65 C. The reaction mixture is stirred first for 30 minutes at -70 C. and then without external cooling until a temperature of +20 C. is reached, then poured into 600 ml of ice water and extracted with 200 ml of ethyl acetate. The organic phase is separated off and the aqueous phase is extracted several times with ethyl acetate. The combined organic extracts are dried with sodium sulphate, evaporated down in vacuo and the residue remaining is recrystallized from diisopropylether. 41.9 g (85% of theory) of 4-(4-dimethylaminomethylphenyl)-4-hydroxycyclohexanone-ethylene ketal are obtained, m.p. 84-86 C.

The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Karl Thomae GmbH; US5726205; (1998); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (7.4 g, 37 mmol) in HC(OMe)3 (100 mL) was added TsOH (0.36 g, 1.9 mmol). The reaction mixture was heated at 100 C for 4 h and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over Na2SO4, and concentrated. The crude product was used in next step without further purification (7.3 g, 93%). LCMS (mlz): 212.1 (M+ 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; SHAPIRO, Gideon; (393 pag.)WO2015/200677; (2015); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromobenzo[c][1,2,5]thiadiazole

To a clear solution of B(C6F5)3 (0.050 g, 0.098 mmol) in CH2Cl2 (5 mL) was added a colorless solution of 4-bromo-benzo[2,1,3]thiadiazole (0.021 mg, 0.098 mmol) in CH2Cl2 (5 mL). The resulting yellow solution was allowed to stir for 30 minutes at room temperature. The solvent was removed in vacuo and the resulting solid washed with pentanes (2.x.10 mL) and dried under vacuum for 1 hour. The product was collected as a faint yellow solid. Recovered yield, 60 mg (85percent). Crystal’s suitable for X-ray diffraction were grown via slow diffusion of pentane into a concentrated solution of 4 in CH2Cl2. Upon addition of excess B(C6F5)3 (3 equivalents total) to 4, no change in the 1H or 19F spectrum was observed from 25 to -50° C. 1H NMR (CD2Cl2): delta 8.02 (d, 3JH-H=8 Hz, 1H, benzothiadiazole-p-CH), 7.71 (dd, 3JH-H=8 Hz, 3JH-H=8 Hz, 1H, benzothiadiazole-m-CH), 7.50 (d, 3JH-H=8 Hz, 1H, benzothiadiazole-o-CH). {1H} NMR (CD2Cl2): delta -5.5 (bs). 13C{1H} NMR (CD2Cl2, -50° C.) partial: 152.79, (s, quaternary), 149.22 (s, quaternary), 148.90 (dm, 1JC-F=250 Hz, CF), 148.22 (dm, 1JC-F=250 Hz, CF), 146.55 (dm, 1JC-F=245 Hz, CF), 141.73 (dm, 1JC-F=245 Hz, CF), 140.85 (dm, 1JC-F=250 Hz, CF), 138.99 (dm, 1JC-F=240 Hz, CF), 137.05 (dm, 1JC-F=245 Hz, CF), 136.74 (s, benzothiadiazole-m-CH), 134.01 (s, benzothiadiazole-p-CH), 131.90 (dm, 1JC-F=250 Hz, CF), 117.22 (quaternary), 116.05 (s, benzothiadiazole-o-CH). 19F NMR (CD2Cl2): delta -125.2 (br, 1F, ortho-C6F5), -131.0 (br, 3F, ortho-C6F5), -135.2 (br, 1F, ortho-C6F5), -137.2 (br, 1F, ortho-C6F5), -154.5 (s, 1F, para-C6F5), -156.5 (br, 2F, para-C6F5), -161.6 (br, 2F, meta-C6F5), 163.8 (br, 4F, meta-C6F5). 19F NMR (CD2Cl2, -50° C.): delta -125.17 (m, 1F, 3JF-F=22 Hz, ortho-C6F5), -130.58 (m, 1F, 3JF-F=21 Hz, ortho-C6F5), -131.42 (m, 2F, 3JF-F=24 Hz, ortho-C6F5), -134.13 (m, 1F, 3JF-F=24 Hz, ortho-C6F5), -137.58 (m, 1F, 3JF-F=24 Hz, ortho-C6F5), -153.99 (m, 1F, 3JF-F=20 Hz, para-C6F5), -155.31 (m, 1F, 3JF-F=20 Hz, para-C6F5), -157.27 (m, 1F, 3JF-F=22 Hz, para-C6F5), -161.28 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -162.91 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -162.74 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -163.33 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -163.77 (m, 1F, 3JF-F=22 Hz, meta-C6F5), -164.03 (m, 1F, 3JF-F=22 Hz, meta-C6F5). UV-vis: lambdamax=355 nm. X-Ray: C24H3B1Br1F15N2S1. Space Group=P-1. Cell: a=10.82(15) , b=11.82(18) , c=12.36(18) , alpha=63.7(3)°, beta=75.1(3)°, gamma=84.1(4)°, V=1369(35) 3. R=0.0432percent, Rw=0.1132percent. GOF=1.027.

According to the analysis of related databases, 22034-13-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bazan, Guillermo C.; Welch, Gregory C.; Coffin, Robert; Peet, Jeff; US2011/28656; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 24358-62-1, 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. 24358-62-1, name is 1-(4-Bromophenyl)ethylamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding ketone (20 mmol, 1.0 eq) and CH3OH (20 mL) were added to a 250 mL Schlenk tube containing [RhCp*Cl2]2 (61.8 mg, 100 mumol, 0.005 equiv) and HCOONH4 (6.36 g, 100 mmol, 5.0eq). The brown mixture was frozen, and the whole system was evacuated. The system was closed and then stirred at 70 C for 7 h. After the dark green resulting solution was cooled to room temperature, 1M aqueous HCl solution (38.4 mL) was added, and the mixture was washed twice with CH2Cl2 (5 mL) to remove the neutral compounds. After addition of a cold 12 M aqueous NaOH solution (3.6 mL) to the aqueous layer, the mixture was extracted six times with CH2Cl2 (12 mL). The combined organic layers were dried over anhydrous Na2SO4. Filtration and evaporation under reduced pressure gave crude amine,which was used without purification. All the crude corresponding amine was dissolved in dichloromethane (50 mL), and TCCA (trichloroisocyanuric acid) (3.2 g, 14 mmol) was added in a250 ml round-bottom flask at 0 C. Then, the mixture was stirred at ambient temperature during 1 h. Triethylamine (6.0 g, 6 mol) dissolved in dichloromethane (50 mL) was added, and the resulting mixture was washed with water (200 mL) and hydrochloric acid (1 M, 200 mL)successively. The organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, purification by column chromatography on silica gel (n-hexane/EtOAc:40/1) afforded pure product.

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-(4-Bromophenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chu, Benfa; Fang, Lili; Guo, Shan; Qi, Bing; Shi, Pengfei; Wang, Qi; Zhu, Jin; Tetrahedron Letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary