Tag: M.W=200-300

Electric Literature of 138526-69-9, A common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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: PN (0.004 mol) was dissolved in anhydrous tetrahydrofuran (10 mL). The solution was added dropwise to the appropriate Grignard reagent (0.006 mol, 1 mol/L in tetrahydrofuran, prepared from respective bromide and magnesium) via a syringe at -40 C. After stirring for 20 min, the reaction was moved to ice-bath and quenched with saturated aqueous solution of ammonium chloride. The aqueous phase was extracted with dichloromethane and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dissolved in dichloromethane and treated with DDQ (0.004 mol). The reaction was refluxed for 3 h, filtered to move the precipitate. The crude product was further purified by column chromatography (petrol ether: ethyl acetate = 5:1) [21].

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Ya-Nan; Feng, Yi-An; Li, Zhong; Shao, Xu-Sheng; Chinese Chemical Letters; vol. 28; 6; (2017); p. 1228 – 1231;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 73918-56-6,Some common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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.

General procedure: The appropriate aldehyde 6a-c and 12a-g (1 mmol) was dissolved in 5 mL of CH2Cl2 in a round bottom flask. Then AcOH (1 mmol) and the appropriate amine (1.1 mmol) were added to the stirring solution at room temperature. The mixture was allowed to stir at room temperature for 20 min before NaBH(AcO)3 (3 mmol) was added. The mixture was allowed to stir at room temperature for overnight. Then,after completion, the reaction was quenched with NaOH 1M solution(15 mL). The mixture was then allowed to stir for 30 min. The reaction mixture was then diluted with EtOAc (10 mL), washed two times with EtOAc (10 mL) and once with brine (20 mL). The organic extracts were collected and then dried over Na2SO4, and the solvent was evaporated to yield the crude compounds 7a-e, 13a-o, 14a-b and 15a which were purified by silica gel column chromatography.

The synthetic route of 73918-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Pingxian; Yang, Yang; Ju, Yuan; Tang, Yunxiang; Sang, Zitai; Chen, Lijuan; Yang, Tao; An, Qi; Zhang, Tianyu; Luo, Youfu; Bioorganic Chemistry; vol. 80; (2018); p. 422 – 432;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1195-33-1, name is 4-Bromobenzenesulfinic acid, 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 1195-33-1, Safety of 4-Bromobenzenesulfinic acid

(a) The 4-(4-bromophenylsulphonyl)-5-methyl-1,2-benzenediol used in the above Example is obtained by oxidative condensation of 76.0 g of p-bromobenzenesulphinic acid (obtained from p-bromobenzenesulphochloride by reduction with sodium sulphite) with 53.0 g of 4-methyl-1,2-benzenediol in a manner analogous to that described in Example 5a), in the form of colourless crystals having a melting point of 190-191.5 (from chloroform).

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

Reference:
Patent; Ciba-Geigy AG; US4600709; (1986); A;,
Bromide – Wikipedia,
bromide – Wiktionary

89359-54-6, name is 9-Bromo-1-nonene, 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. SDS of cas: 89359-54-6

Example 28 This example illustrates the synthesis of 1-(8-Nonenyl)glutarimide (CT1604). Sodium hydride (1.02 g, 44 mmol) was added to a solution of glutarimide (5.00 g, 44 mmol) in dimethyl sulfoxide (150 ml). After 20 min of stirring, 9-bromo-1-nonene (9.02 g, 44 mmol) was added. After 16 hr of stirring at room temperature, the reaction was poured into a separatory funnel containing 100 ml water and extracted with dichlormethane (3*70 ml). The organic portions were combined, washed with water (2*40 ml) and brine (50 ml) and dried to give the olefin CT1604 as a colorless oil (10.09 g, 97% yield).

The synthetic route of 89359-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cell Therapeutics, Inc.; US5521315; (1996); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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 337915-79-4, name: 5-Bromo-N1-methylbenzene-1,2-diamine

Example 45 4- ( (4-Chlorobenzyl) oxy) -1- (l-methyl-2- (trifluoromethyl) -1H- benzimidazol-6-yl) pyridin-2 (1H) -one A) 6-Bromo-l-methyl-2- (trifluoromethyl ) -lH-benzimidazole The mixture of 5-bromo-N1-methylbenzene-l, 2-diamine (300 mg) and TFA (10 ml) was stirred at 90C overnight. The mixture was quenched with saturated NaHC03 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04, passed through NH silica gel pad and concentrated in vacuo. The precipitate was collected by filtration, washed with IPE/hexane and dried in vacuo to give the title compound (265 mg) as a purple solid. MS (ESI+) : [M+H] + 280.9.

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, 5-Bromo-N1-methylbenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 615-55-4,Some common heterocyclic compound, 615-55-4, name is 3,4-Dibromoaniline, molecular formula is C6H5Br2N, 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 21 3-Chloro-N-(3,4-dibromophenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine, having a melting point of about 166-167 C., weighing 2.4 g., from 5 g. of 3,4-dibromoaniline and 3 g. of 2,4-dichloro-3,5-dinitrobenzotrifluoride.

The synthetic route of 615-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US4152460; (1979); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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. Product Details of 937046-98-5

To a degassed solution of 7-bromopyrrolo[2,1-f][1 ,2,4]triazin-4-ylamine (10.0 g, 46.9 mmol) in anhydrous DMF (78 ml_) and triethylarnine (47 mL) was added tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol, 0.04 eq) and copper (I) bromide dimethylsulfide complex (0.77 g, 3.75 mmol, 0.08 eq). After degassing with N2 for 5 min., propargyl alcohol (8.2 mL, 140.8 mmol, 3.0 eq) was added, and the reaction mixture was stirred at 900C for 6h. The reaction was quenched with 5% aq. NH3 in saturated aq. NH4CI. The aqeuous layer was washed with EtOAc (1x) followed by 25% iPrOH in DCM (3x). The combined organic layers were dried over MgSO4, filtered through a pad of Celite, and concentrated at reduced pressure. The crude product was purified by MPLC eluted with 5% EtOH/DCM. Trituration from EtOAc afforded 4.75 g (53.8%) of the desired product as a yellow solid. 1H-NMR (DMSO-alphafe) .67.89 (s, 1 H), 7.88 (broad s, 2H), 6.85 (dd, 2H), 5.39 (t, 1H), 4.36 (d, 2H); LC-MS [M+H]+ = 189, RT = 1.08 min.

The synthetic route of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
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 33070-32-5 as follows. HPLC of Formula: C7H3BrF2O2

Magnesium turnings (11.12g, 0.464mol) and anhydrous tetrahydrofuran (600 ml) were placed in a round-bottomed flask fitted with a mechanical stirrer, reflux condenser, pressure equalizing addition funnel and drying tube. 5-Bromo-2,2- difluoro-l,3-benzodioxole (lOOg) was added to the flask under nitrogen atmosphere. The temperature of the reaction mass was raised to 40C during initiation. Upon initiation, remaining 5-Bromo-2,2-difluoro-l,3-benzodioxole (lOOg) was added drop- wise to the reaction mass. The temperature of the reaction mass was maintained below 40C. The progress of the reaction was monitored by gas chromatography. The reaction mass was then cooled to 0C and carbon-dioxide gas was passed for 2 hours at 0C. The raction was monitored by liquid chromatography for completion. The reaction mass was quenched with 10% HC1 (230g). The organic layer was separated, concentrated to obtain solid. The solid was washed with water (50g) and dichloromethane (50g), filtered and dried at 60C under 50mmHg for 2 hours to obtain the title compound. Yield (%): 70 Purity (%): 99 (by liquid chromatography)

According to the analysis of related databases, 33070-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SRF LIMITED; KUMARASAMY, Radha; RAJARAM, Aiyswariya; GANESAN, Varadharaj; RAVICHANDRAN, Poornachandran; BOKKA, Deepak; KAVERIKKANNAN, Nagarajan; BASHA, Thurabudin Mohamed Kaleel; SEETHARAMAN, Prasannakumar; MARI, Chandra Mohan; KUMAR, Kapil; ANAND, Rajdeep; (15 pag.)WO2017/46816; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 33070-32-5, 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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. 1 -(2 ,2-Difluoro-benzor 1,31 dioxol-5 -vD-cyclopropanecarboxylic acid; Step a: 2,2-Difluoro-benzofl ,3] ‘dioxole-5-carboxylic acid methyl ester; A solution of 5-bromo-2,2-difluoro-benzo[l,3]dioxole (11.8 g, 50.0 mmol) and tetrakis(triphenylphosphine)palladium (0) [Pd(PPh3 )4, 5.78 g, 5.00 mmol] in methanol (20 mL) containing acetonitrile (30 mL) and triethylamine (10 mL) was stirred under a carbon monoxide atmosphere (55 PSI) at 75 0C (oil bath temperature) for 15 hours. The cooled reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by silica gel column chromatography to give crude 2,2-difluoro-benzo [1,3] dioxole-5- carboxylic acid methyl ester (11.5 g), which was used directly in the next step.

The synthetic route of 5-Bromo-2,2-difluorobenzodioxole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/141119; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 337915-79-4,Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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 intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCI2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and 1N NaOH (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compound was obtained as a cream powder (2.5g, 54.74%); m.p. 126-128C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/111036; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary