Month: July 2021

Synthetic Route of 142808-15-9, 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. 142808-15-9 name is 4-Bromo-2-fluorobenzotrifluoride, 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.

Example 28 Preparation of 1-bromo-3-fluoro-2-methyl-4-(trifluoromethyl)benzene To a stirred solution of bis(isopropyl)amine (1.383 mL, 9.87 mmol) in THF (27.4 mL) at -78 C. was added n-butyllithium (3.62 mL, 9.05 mmol). The resulting pale yellow solution was stirred at -78 C. for 15 min, warmed to 0 C. for 15 min, then recooled to -78 C. for 15 min. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (2 g, 8.23 mmol) was then added, and the resulting solution was stirred at -78 C. for 2 h. Iodomethane (0.512 mL, 8.22 mumol) was then added. The solution was allowed to slowly warm to room temperature (rt) and stirred overnight. The reaction mixture was diluted with 0.1 M hydrochloric acid (HCl) and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude brown residue was purified via flash chromatography on silica (5-30% ethyl acetate (EtOAc)/Hexanes) to yield the title compound as a clear oil (1.7 g, 80%): 1H NMR (400 MHz, CDCl3) delta 7.57-7.41 (m, 1H), 7.32-7.26 (m, 1H), 2.41 (dd, J=10.0, 8.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) delta -61.2, -105.7, -108.1; IR (thin film) 2177, 1319 cm-1.

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

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); 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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H5BrF3N

Production Example 62N- [3-{2- [4- (hydrazinocarbonylmethyl) phenyl] ethyl}-2-(trifluoromethyl) phenyl] acetamide hydrochlorideUsing N7 [3-bromo-5- (trifluoromethyl) phenyl] acetamide obtained by treating 3-bromo-5- (trifluoromethyl) aniline with acetic anhydride as a starting material, the title compound was synthesized by a method similar to Production Example 1, steps 4 – 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; R-tech Ueno, Ltd.; WO2009/145360; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 74586-53-1, The chemical industry reduces the impact on the environment during synthesis 74586-53-1, name is 3-Bromo-5-methylaniline, I believe this compound will play a more active role in future production and life.

To a stirring solution of 3-bromo-5-methylaniline (5.00 g, 26.9 mmol) in THF (100 mL) was added K2CO3 (11.14 g, 81 mmol) followed by 2-chloroethyl chloroformate (4.16 mL, 40.3 mmol) and the resulting reaction mixture was refluxed for 4 h. The reaction mixture was cooled to ambient temperature, diluted with 5% NaHCO3 solution (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain Intermediate 76A (7.00 g, 89.00%) as a white solid. 1H NMR (300 MHz, DMSO-d6) G^ppm 2.25 (s, 3 H), 3.81 – 3.95 (m, 2 H), 4.32 – 4.42 (m, 2 H), 7.04 (s, 1 H), 7.26 (s, 1 H), 7.55 (s, 1 H), 9.96 (s, 1 H). LCMS (Method-D ): retention time 2.99 min, [M+H] 291.0.

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, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 58971-11-2, A common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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 mixture of 3-bromobenzeneethanamine (2.00 g, 10.0 mmol) and 2,6-lutidine (1.2 mL, 10.3 mmol) in dry CH2C12 (40 mL) was cooled to 0 C. Trifluoroacetic anhydride (1.4 mL, 9.9 mmol) was added dropwise, and the reaction was then warmed to room temperature and allowed to stir for 16 h. Water (40 mL) was added to the reaction, the phases were separated, and the aqueous layer was extracted with CHZCLZ (2 x 40 mL). The combined organic phases were washed successively with 1 M HCl (40 mL) and saturated NAHC03 (40 mL), and then dried over NazS04, filtered, and concentrated in vacuo to provide the title compound (2.93 g, 100%). The crude compound was used in subsequent steps. 1H-NMR (CDCl3): 8 7.40 (d, J=8. 0 Hz, 1H), 7.36 (s, 1H), 7.21 (t, J=7. 6 Hz, 1H), 7.12 (d, J=7. 6 Hz, 1H), 6.33 (br s, 1H), 3.59 (q, J=6. 8 Hz, 2H), 2.87 (t, J=7. 2 Hz, 2H). MS (ESI) (M+H) += 296/298.

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/60882; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1073-06-9, 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Magnesium chips (13.2 g) were placed into a 1L flask equipped with mechanical stirrer, nitrogen inlet, 500 ml pressure-equilibrated dropping funnel, thermometer and reflux condenser connected to the inert gas outlet. The flask was flushed with nitrogen and minor flow was held during whole reaction time. 1-Bromo-3-fluorobenzene (95 g, 0.542 mol) and dry tetrahydrofurane (300 ml) was placed in dropping funnel. Magnesium was moistened with few milliliters of the solution from dropping funnel and an iodine crystal was added. When exothermic reaction starts 1-bromo-3-fluorobenzene solution was added dropwise to keep the boiling temperature of the mixture. After dropping all of the solution, the mixture was refluxed for 2 hours. Then the mixture was cooled down to -78 C. in a dry ice/acetone bath and propionaldehyde was added dropwise while mixture temperature was kept below -70 C. After adding all of the aldehyde, the mixture was left overnight at room temperature. Then the tetrahydrofurane was evaporated and the residue was acidified with hydrochloric acid. The organic phase was separated, washed twice with water and dried over magnesium sulfate. The raw 1-(3-fluorophenyl)propanol was distilled under reduced pressure of 20 mbar at 117 C. Alcohol 60 g, 66% of theor. yield was obtained. The alcohol and toluene (250 ml) and p-toluenesulfonic acid (0.2 g) were placed in (500 ml) round-bottom flask equipped with Dean-Stark trap. The mixture was refluxed. After the water stopped appearing, toluene was evaporated at reduced pressure. The obtained 1-(3-fluorophenyl)propene was placed in a three-necked flask and acetic acid (30 ml), ethyl acetate (50 ml) and catalyst-palladium on active carbon (2 g) were added. The flask was filled with hydrogen from gas burette at room temperature and the mixture was stirred. Reaction temperature increased spontaneously to 30 C. When the absorption of hydrogen was stopped, the catalyst was filtered off, the solution was washed off with water, dried over MgSO4 and the solvent was evaporated. The 1-fluoro-3-propylbenzene was distilled under atmospheric pressure, collecting the fraction boiling at 160 C. 32 g of 1-fluoro-3-propylbenzene were obtained, 42% of theor. yield.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dabrowski, Roman Slawomir; Kula, Przemyslaw; Choluj, Artur; Dziaduszek, Jerzy; Garbat, Katarzyna; US2013/20532; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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 630-17-1, Quality Control of 1-Bromo-2,2-dimethylpropane

Intermediate 7A: 6-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid; Step 1 Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate: To a stirred solution of Intermediate 6 (1.60 g, 4.209 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added cesium carbonate (2.74 g, 8.418 mmol) followed by 1-bromo-2,2-dimethylpropane (1.60 mL, 12.629 mmol) at room temperature. The resulting suspension was stirred at 110 C. overnight under nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (200 mL) and water (100 mL). The layers were separated. Aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with brine (2×50 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue obtained after the evaporation of the solvent was purified by silica gel column chromatography using 10% ethyl acetate in petroleum ether to obtain 1.20 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) delta 1.07 (s, 9H), 1.39 (t, J=6.9 Hz, 3H), 3.57 (s, 2H), 4.35-4.42 (m, 2H), 7.18 (t, J=74.7 Hz, 1H), 7.20-7.25 (m, 2H), 7.47 (d, J=3.9 Hz, 1H), 7.52-7.58 (m, 1H), 7.73 (d, J=16.2 Hz, 1H), 7.90 (d, J=16.2 Hz, 1H), 8.10-8.16 (m, 1H); APCI-MS (m/z) 451.10 (MH)+.

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

Reference:
Patent; Glenmark Pharmaceuticals S.A; US2010/152192; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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: C6H3BrF2

-Bromo-1,4-difluorobenzene (53.6 g, 277.74 mmol) in THF (50 ml) was cooled to -50 C., to it was added isopropyl magnesium chloride (2M in THF) (133 mL, 266 mmol). The reaction mixture thus obtained was warmed to 0 C. and stirred for 1 h. The reaction mixture was cooled again to -50 C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200 mL) was added drop wise to this reaction mixture with stirring and the stifling was continued at 0 C. for 1 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution, extracted with ethylacetate. The organic layer collected was washed with water (500 mL) and then with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude liquid residue. The residue thus obtained was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent) to afford 35 g of the title compound as a colorless liquid. 1H NMR (300 MHz, CDCl3) delta 7.60-7.53 (1H, m), 7.26-7.09 (2H, m), 3.70 (2H, t), 3.22-3.14 (2H, m), 2.28-2.16 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 399-94-0, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; Sasmal, Pradip Kumar; Ahmed, Shahadat; Tehim, Ashok; Paradkar, Vidyadhar; US2015/368238; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 86845-27-4, 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. 86845-27-4, name is 5-Bromo-2-methylbenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

III.2; [4-bromo-2-(trifluoromethyl)phenyl] acetonitrile; Step 1 : 4-bromo-l-(bromomethyl)-2-(trifluoromethyl) benzene; A solution of commercially available 4-bromo-l -methyl -2 -(trifiuorornethyl)benzene (1 eq.), NBS (1.1 eq.) and a catalytic amount of benzoyl peroxide in CCl4 (0.21M) was stirred at room temperature for Ih under a 150W spot lamp. The mixture was concentrated, purification by column chromatography on silica gel, eluting with Hex, afforded the desired material as an oil.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-methylbenzotrifluoride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/23964; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3, 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. 54962-75-3 name is 3-Bromo-5-(trifluoromethyl)aniline, 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.

3-Bromo-5-(trifluoromethyl)aniline (5.0 g) and 1,4-dibromobutan-2-ol (4.83 g) were stirred at 100 C. for 3 hr. After cooling to room temperature, to the reaction mixture was added saturated aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50) to give the title compound (5.6 g, yield 22%) as a brown oil.1H-NMR (300 MHz, CDCl3) delta: 1.66 (br. s, 1H), 2.08-2.27 (m, 2H), 3.23-3.32 (m, 1H), 3.38 (td, J=8.8, 3.4 Hz, 1H), 3.44-3.59 (m, 2H), 4.65 (br. s, 1H), 6.65 (s, 1H), 6.80 (t, J=1.9 Hz, 1 H), 7.02 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1798-85-2,Some common heterocyclic compound, 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene, molecular formula is C9H9Br, 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 stirred suspension oflntermediate B-4 (201.8 mg, 0.647 mmol), 1-bromo-3-cyclopropylbenzene (246.7 mg, 1.252 mmol), Pd2(dba)3 (58.5 mg, 0.064 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (“X-Phos”) (30.7 mg, 0.064 mmol)and potassium carbonate (414.7 mg, 3.00 mmol) in t-BuOH (4.0 mL) was degassed(pump/N2 x 3) and then heated to 80 oc overnight. The reaction mixture was cooled to20 room temperature. The mixture was diluted with EtOAc, filtered through a 4 )lmmembrane filter, concentrated, and then dried under vacuum. The residue was purifiedby flash chromatography (Teledyne ISCO CombiFlash Rf, gradient ofO% to 100% using solvent A/B=heptane/EtOAc over 15 column volumes, REDISEP Si02 40g, loaded asDCM solution). Obtained Intermediate B-12A (134.0 mg, 48%) as a tan solid: HPLC_RT=2.218 min (Waters SunFire C18 2.1x30mm, MeOH/H20/0.1% TFA, 2min gradient,wavelength= 254 nm); MS(ES): m/z= 372/374 [M-t-Bu+ It; 1H NMR (400 MHz,5 chloroform-d) 8 7.05-7.15 (m, IH), 6.59 (d, J=7.70 Hz, IH), 6.47-6.55 (m, 2H), 5.61 (d,J=7.26 Hz, IH), 4.53-4.65 (m, IH), 4.26-4.33 (m, IH), 3.66 (dd, J=9.57, 11.77 Hz, IH),1.75-1.85 (m, IH), 1.46 (s, 9H), 0.85-0.97 (m, 2H), 0.57-0.71 (m, 2H).

The synthetic route of 1798-85-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILL, Patrice; QUESNELLE, Claude A.; SAULNIER, Mark G.; GAVAI, Ashvinikumar V.; WO2014/47369; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary