Month: September 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 2695-47-8 as follows. Computed Properties of C6H11Br

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

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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. Computed Properties of C6H11Br

Example 8A 2-(Trimethylsilyl)ethyl (1RS,2RS,5SR)-2-[4-(cyclopentylmethoxy)benzoyl]-5-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]cyclopentanecarboxylate (racemate) To a solution of 80 mg (0.16 mmol) of the compound from Example 4A in 1.8 ml of acetonitrile were added 45 mg (0.32 mmol) of potassium carbonate and 32 mg (0.19 mmol) of (bromomethyl)cyclopentane, and the mixture was stirred under reflux overnight. Thereafter, a further 32 mg (0.19 mmol) of (bromomethyl)cyclopentane were added, and the mixture was stirred under reflux once again for 4 h. After cooling to RT, the mixture was diluted with water and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by means of preparative HPLC (Method 7). 33 mg (36% of theory, 100% purity) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.61 min, m/z=576 [M+H]+.

The synthetic route of (Bromomethyl)cyclopentane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (91 pag.)US2017/22171; (2017); A1;,
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. 583-75-5, name is 4-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-2-methylaniline

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl-2,2,4,8-tetramethylquinoline (Compound 292, Structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 -nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70 g). Most of the aniline (>80%) was recovered.

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 583-75-5.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature 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

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. category: bromides-buliding-blocks

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 112734-22-2, The chemical industry reduces the impact on the environment during synthesis 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, I believe this compound will play a more active role in future production and life.

To a solution of ethyl 2-((2-fluorobenzyl)oxy)-4-formylnicotinate (2.10 g) obtained in Reference Example 183 and (4-bromo-2-fluorophenyl)methanamine (1.48 g) in methanol (13 mL)-THF (13 mL) was added magnesium sulfate (1.67 g) at room temperature, and the mixture was stirred under a nitrogen atmosphere at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was concentrated. To a solution of the residue in acetic acid (13 mL) was added sodium triacetoxyhydroborate (2.20 g) at room temperature, and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (1.06 g). MS: [M+H]+ 445.0 1H NMR (300 MHz, CDCl3) delta 4.32 (2H, s), 4.76 (2H, s), 5.67 (2H, s), 6.93-7.20 (3H, m), 7.22-7.38 (4H, m), 7.71 (1H, t, J = 7.4 Hz), 8.27 (1H, d, J = 5.1 Hz).

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, (4-Bromo-2-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 51436-99-8, 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. 51436-99-8 name is 4-Bromo-2-fluorotoluene, 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.

Dried magnesium turnings (4.24 g, 0.55 mole) were stirred with a heavy stirrer bar under argon for 16 hours. A few crystals of iodine were added followed by a solution of 4-bromo-2- fluorotoluene (94.5 g, 0.5 mole) in tetrahydrofuran [THF] (200 ml). This addition took place over about 40 minutes and the solution was allowed to reflux during the addition. The resulting solution was stirred for 1 hour. 4-Bromobenzaldehyde (71.7 g 0.39 mole) in THF (200 ml) was cooled to 0C then treated with the above Grignard solution. The addition of the Grignard solution took place over 30 minutes and the resulting solution was stirred for 2 hours at room temperature. The reaction mixture was poured slowly into a solution of potassium sodium tartrate (10% solution, 1 L) and extracted with ethyl acetate (EtOAc). The organic solution was dried with brine and sodium sulfate and evaporated. Trituration with hexane gave the title compound (D1) as a white solid (71.8 g, 65%).’H NMR: 8 CDCI3 2.20 (1H, d), 2.24 (3H, m), 5.75 (1H, d), 6.98 (1H, s) 7.05 (1H, m), 7.16 (1H, m), 7.24 (2H, m) 7.47 (2H, m).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/51397; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 57190-17-7, name is 2-Bromo-1,3-diisopropylbenzene, 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 57190-17-7, name: 2-Bromo-1,3-diisopropylbenzene

To a flask was added o-phenyldiamine (0.17 g, 1.6 mmol), (1-Bromo-2,6-diisopropylbenzene) (0.31 g, 1.3 mmol), Pd(t-Bu3P)2 (0.082 g, 0.16 mmol), NaOtBu G, 3.2 mmol) and toluene (11 mL). Reflux at 100C for 3 hours; The reaction mixture was cooled, filtered using dry silica, and washed with ethyl acetate. After drying all the solvent, the compound 1a was separated by Hx: EA = 4: 1 using column chromatography to obtain Compound 1a (0.21 g, 60%).

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, 2-Bromo-1,3-diisopropylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG Chemical Co., Ltd.; Lee, Hay Gyung; Jeon, Sang Jin; Lee, In Sun; Jung, Jae Yeop; (18 pag.)KR2015/85626; (2015); A;,
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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-3-(tert-butyl)benzene

A 1.6M solution of”butyllithium (1.7 mL, 2.72 mmol) was added to a solution of dicyclohexylamine (0.52 mL, 2.61 mmol) in toluene (10 mL). After stirring for 5 min, a mixture of cisltrans isomers of 4-methyl-cyclohexanecarboxylic acid methyl ester (342 mg, 2.19 mmol) was added. After stirring for 10 min, 1-bromo-3-tert- butyl-benzene (428 mg, 2.01 mmol) and bis (tri-tert-butylphosphine) palladium (0) (52 mg, 102 umol) was sequentially added. After stirring for 20 h, the solution was diluted with 10percent aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49: 1,24 : 1, and 23: 2 hexanes: ethyl acetate as the eluant to yield 484 mg (84percent yield) of a mixture of cisltrans isomers of 1- (3-tert-butyl-phenyl)-4-methyl-cyclohexanecarboxylic acid methyl ester as a light yellow oil. 1H NMR (300 MHz, CDC13) b 7.51 and 7.40 (t and m, J=1.9 Hz, 1H), 7.33-7. 13 (m, 3 H), 3.65 (s, 3 H), 2.62 (m, 2H), 1.77-1. 02 (broad m, 7 H), 1.30 (s, 9H), 0.91 (d, J=6.5 Hz, 3 H).

The synthetic route of 3972-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87751; (2005); A2;,
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. Quality Control of 1-Bromocyclohex-1-ene

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