Month: June 2021

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. 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-4-fluoro-2-methylbenzene

Intermediate 2:; 4-Fluoro-2-methvl-benzaldehvde; 2-Bromo-5-fluorotoluene (15.0 g, 79.3 mmol) was dissolved in anhydrous THF andcooled to -78C in an acetone/dry ice bath. N-butyl-lithium (48.0 mL, 119 mmol) was addeddropwise down the side of the reaction flask and the resulting solution was stirred for 10 min. 64.0 ml of anhydrous DMF (793 mmol) was then added in the same fashion. After 1 hour, the reaction was quenched with cold aqueous NH4CI and diluted with 500 mL Et2O and washed with water (3x 300 mL)., The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude material was then equipped with a distillation apparatus and the oil bath was heated to 110 C. Product containing fractions were collected to give a colorless oil, (10.0 g , 72.4 mmol, 92% yield); LRMS m/z (APCI+) 139 [M+ H]; 400 MHz 1HNMR (CDCI3) 8 10.91 (s, 1H); 7.81 (dd, J=6.2, 2.5 Hz, 1H); 7.03 (ddd, J=8.2, 8.2, 2.5 Hz, 1H); 6.95 (ddd, J=9.5, 2.5, 0.0 Hz, 1H); 2.67 (s, 3H).

According to the analysis of related databases, 452-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/110996; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1647-26-3, The chemical industry reduces the impact on the environment during synthesis 1647-26-3, name is 1-Bromo-2-cyclohexylethane, I believe this compound will play a more active role in future production and life.

General procedure: The product from Example 32A (0.046 g, 0.2 mmol), 2-(bromomethyl)pyridine hydrobromide (0.066 g, 0.260 mmol), and potassium carbonate (0.069 g, 0.500 mmol) were combined in dimethylformamide (1.0 mL) and stirred for 16 hours. The reaction mix was partitioned between ethyl acetate and water. The organic layer was separated and concentrated. Purification by chromatography (silica gel, 0-4% methanol in dichloromethane) afforded the title compound (0.030 g, 46%). Example 42 was prepared according to the procedure of Example 40 substituting (2- bromoethyl)cyclohexane for 2-(bromomethyl)pyridine hydrobromide and heating the reaction mixture at 50 C for 6 hours. Purification by chromatography (silica gel, 0-100% ethyl acetate in hexane) afforded the title compound (0.038 g, 63%). 1H NMR (300 MHz, DMSO-d6) delta 7.35 – 7.45 (m, 1 H) 7.21 (dd, J=7.54, 1.59 Hz, 1 H) 7.07 (d, J=7.54 Hz, 1 H) 6.98 (t, J=7.93 Hz, 1 H) 6.36 (s, 1 H) 3.97 (t, J=6.35 Hz, 2 H) 3.71 (s, 3 H) 3.60 (s, 3 H) 1.56 – 1.67 (m, 5 H) 1.46 (q, J=6.61 Hz, 2 H) 1.03 – 1.36 (m, 4 H) 0.72 – 0.98 (m, J=l l .l l Hz, 2 H). MS (ESI+) m/z 343 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI)COMPANY, LTD.; HUBBARD, Robert Dale; MCDANIEL, Keith F.; PARK, Chang Hoon; PRATT, John K.; SOLTWEDEL, Todd; SUN, Chaohong; WANG, Le; WENDT, Michael D; WO2013/185284; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

3638-73-1, name is 2,5-Dibromoaniline, 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. Formula: C6H5Br2N

The 2,5-dibromo-aniline (3.74g, 14.9mmol), 4- methoxycarbonyl phenyl boronic acid (8.08g, 44.9mmol), palladium acetate (240mg, 1.07mmol) placed in 250mL round bottom flask, then added 40mLN , of N- dimethylformamide solvent, the addition of sodium carbonate (5.66g, 44.9mmol) was dissolved in 46mL of water dubbed aqueous sodium carbonate, aqueous sodium carbonate was added to the above 250mL round bottom flask. Then under nitrogen at a temperature of 60 , 18 hours. After the reaction was cooled to room temperature, suction filtered and washed with copious amounts of water. With ethyl acetate (100mL × 3) after the spin dry the solid solvent extraction, and finally washed with acetone to give the product as a gray solid.

The synthetic route of 3638-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan University; Wang, Cheng; Meng, Xiangshi; Gui, Bo; (12 pag.)CN105503929; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1435-51-4, A common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

General procedure: Palladium reagents were synthesized following the scheme of Figure 14 for generalprocedure A. In a nitrogen-filled glovebox, an oven-dried scintillation vial (1 0 mL), whichwas equipped with a magnetic stir bar and fitted with a Teflon screwcap septum, vascharged with RuPhos (2.5 equiv), a dihaloaryl compound (1 equiv) and cydohexane (1.2mL). Solid [(1,5-COD)Pd(CH2Si:Me3)] (2.5 equiv) was added rapidly in one portion and theresulting solution vvas stirred for 16 hat Jt. After this time, pentane (3 mL) was added andthe resulting mixture vas placed into a -20 C freezer for 3 h. The vial was then takenoutside of the glove box, and the resulting precipitate was filtered, washed with pentane (3 X3 mL), and dried under reduced pressure to afford the oxidative addition complex (Figure14)

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; BUCHWALD, Stephen, L.; PENTELUTE, Bradley, L.; ZHANG, Chi; (170 pag.)WO2017/151910; (2017); A2;,
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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., COA of Formula: C7H8BrN

To a solution of commercially available 3-bromo-benzylamine (938 mg) in dry dichloromethane (10 mL) was added added di-tert-butyl dicarbonate (1.10 g). The resulting clear solution was stirred at room temperature for 15 h and then concentrated to afford the title compound (1.42 g; 99%). [(M-isobutene)H]+=230/232, [MNa]+=308/310.

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; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 61326-44-1,Some common heterocyclic compound, 61326-44-1, name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, molecular formula is C26H16Br4, 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.

The present invention is preferably 1,1,2,2-tetrakis(4-bromophenyl)ethylene: 1H-1,2,4-triazole: potassium carbonate: copper oxide molar ratio of 2: 10-15: 30: 1; Reaction temperature of 100 deg.C. The reaction time was 48 hours. In a polar solvent, using the “one-pot method”, 1,1,2,2-tetrakis(4-bromophenyl)ethylene,1H-1,2,4-triazole, potassium carbonate and copper oxide under heating conditions 1,1,2,2-tetrakis[4-(1H-1,2,4-triazol-1-yl)phenyl]ethylene (L) is prepared. Yield 60percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,2,2-Tetrakis(4-bromophenyl)ethene, its application will become more common.

Reference:
Patent; Tianjin Normal University; Wang, Ying; (12 pag.)CN105669705; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

52997-43-0, name is 7-(Bromomethyl)pentadecane, 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. Safety of 7-(Bromomethyl)pentadecane

Di-tert-butyl thieno[3,2-b]thiophene-3,6-diyldicarbamate (20) (0.93 g, 2.5 mmol, 1.0 e.q.) wasdissolved in DMF (25 mL) and cooled to 0C. Sodium hydride (0.40 g, 60% dispersion in mineral oil, 10.0 mmol, 4.0 e.q.) was added and the solution was stirred at room temperature for 1hour. 7-(bromomethyl)pentadecane (2.29 g, 7.5 mmol, 3.0 e.q.) was added to the mixture and the solution was stirred at 80C for 3 hours. After the solution cooled to room temperature, the mixture was poured into iced water, followed by extraction with ethyl acetate for three times.The organic layers were combined, washed with water, brine and then dried over Mg504, concentrated. The resulting brown oil was purified via silica gel column chromatography with di15 chloromethane/petroleum ether (1:1) as the eluentto give di-tert-butyl thieno[3,2-b]thiophene-3,6-diylbis((2-hexyldecyl)carbamate) as a light brown oil (21) (1.64 g, 2.0 mmol, 80 % yield). 1HNMR (400 MHz, CDCI3) 67.04 (s, 2H), 3.62 (d, J= 7.2 Hz, 4H), 1.58-1.48 (m, 2H), 1.34-1.11(m, 48H), 0.87 (q, J= 6.8 Hz, 12H). 13C NMR (101 MHz, CDCI3) 6 154.13, 134.76, 133.70,119.18, 80.64, 53.38, 36.93, 31.90, 31.77, 31.21, 30.03, 29.68, 29.52, 29.29, 28.15, 26.31,26.25, 22.66, 22.62, 14.08.

The synthetic route of 52997-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; FLORES, Jean-Charles; HAYOZ, Pascal; MCCULLOCH, Iain; ONWUBIKO, Nkechinyerem; KAELBLEIN, Daniel; (65 pag.)WO2017/148864; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 583-70-0, A common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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 dried round-bottom flask containing stir bar was charged with magnesium (530 mg, 21.70 mmol), small piece of iodine and dry THF (73 mL) was added under argon. Solution of 1-bromo-2,4-dimethylbenzene (3.65 g, 19.72 mmol) diluted in dry THF (3 mL) was added dropwise to the suspension and the solution was stirred at 50C for 60 mm. After the formation of Grignard reagent,_the_reaction_mixture_was_cooled_to_0C,_and_then_N-[(3-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide Ex.83a (3.37 g, 13.81 mmol) in dryTHF (3 mL)was added dropwise. The resulting mixture was stirred at rt. After the completion of the reaction, the reaction mixture was quenched with sat. NH4CI and the solution was extracted with EtOAc. The combined organic layers were washed with brine. After phases separation, the organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of Hexanes/EtOAc from [90:10] to [60:40] to afford N-[(3-chlorophenyl)(2,4-dimethylphenyl)methyl]-2- methylpropane-2-sulfinamide Ex.83b (2.30 g, 48%) as yellow oil. 1 H NMR (400 MHz, DMSO-d6, din ppm): 1.11 (s, 9H), 2.22 (s, 3H), 2.26 (s, 3H), 5.67 (d, 1H, J=6.3Hz), 6.03 (d, 1H, J=6.3Hz), 6.98 (s, 1H), 7.04 (d, 1H, J=8.OHz), 7.19-7.27 (m, 1H), 7.26-7.40 (m, 4H).

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; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 2044-08-8, name is 1-Bromocyclohex-1-ene, molecular formula is C6H9Br, 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: C6H9Br

Under nitrogen protection, 20 g (0.12 mol) of 1-bromo-1-cyclohexene and 34.7 g (0.14 mol) of pinacol borate were added to the three-necked flask.2.0 g (6 mol%) of triphenylphosphine,2.6 g (3 mol%) of trans-bis(triphenylphosphine)palladium(II) dichloride,Potassium phenolate 24.6 g (0.19 mol) and anhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Purified by silica gel column or distillation21.9 g (yield: 85%) cyclohexene-1-boronic acid pinacol ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2044-08-8, its application will become more common.

Reference:
Patent; Yurui (Shanghai) Chemical Co., Ltd.; Zheng Xianzhe; (52 pag.)CN109206458; (2019); A;,
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 2695-47-8 as follows. Quality Control of 6-Bromo-1-hexene

Step 1: Preparation of 2,2,2-trifluoro-iV-(hex-5-enyl)-N-rnethylacetarnide 11a; Sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added under nitrogen atmosphere to a solution of N-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL) at 0 0C. The reaction mixture was stirred for 90 min at 0 0C, and then 6- bromo-1-hexene (100 g, 1 eq.) was added dropwise over 45 min. The reaction mixture was allowed to warm up to room temperature, and stirred for 3 days at room temperature. The reaction mixture was then poured into water and extracted tree time with EtOAc. The combined organics layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to produce compound 11a as colorless oil in 56% yield.1H NMR (DMSO-^5, 400 MHz) delta 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2.00-2.06 (m, 2H), 2.93-3.07(2m, 3H), 3.35-3.40 (m, 2H), 4.92-5.04 (m, 2H), 5.73-5.83 (m, IH).

According to the analysis of related databases, 2695-47-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; WO2009/14730; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary