Tag: M.W=200-300

35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, belongs to ethers-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. Computed Properties of C11H15BrO2

General procedure: In a 200 mL three necked flask equipped with a dropping funnel, a THF solution of S2 (1.0 equiv.)was slowly added to a mixture of Mg (1.1 equiv., pre-activated by stirring for several hours in vacuo)and THF. A THF solution of alkyne (1.1 equiv.) was subsequently added, and the reaction mixturewas stirred at room temperature. Then, HCl aq. (1M) was added, and the resultant solution wasextracted with Et2O. The organic layer was washed with Brine, dried over anhydrous Na2SO4,filtered, and concentrated in vacuo to yield a crude product including S3. If needed, the purificationwas performed by a column chromatography on a silica gel (eluted with 510% EtOAc/hexane).

The synthetic route of 35822-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hoshimoto, Yoichi; Kumar, Ravindra; Nishimura, Chika; Ogoshi, Sensuke; Sasaoka, Yukari; Bulletin of the Chemical Society of Japan; vol. 93; 2; (2020); p. 182 – 186;,
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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H9BrO

A mixture of compound (III) (Pgi = Pg2 = Cbz) (973 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), 1,10-phenanthroline (36 mg, 0.20 mmol), Cs2CO3 (716 mg, 2.20 mmol), 1-bromo-4- phenoxybenzene (548 mg, 2.20 mmol) and xylene (10 ml) was heated in a sealed tube under argon atmosphere at 140C for 16 h with intensive stirring. After completion of the reaction the tube was cooled to room temperature, carefully opened, and the reaction mass was poured into EtOAc (40 ml). After intensive stirring for 5 mm the obtained suspension was filtered through celite un evaporated in vacuum. The product was purified by column chromatography (eluent EtOAc-hexane 1:2, Rf 0.4). Yield 995 mg (76%), white amorphous powder.

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; LEBEDEVS, Antons; PONOMARJOVS, Jurijs; VARACEVA, Larisa; CERNAKS, Dmitrijs; CERNOBROVIJS, Aleksandrs; LAVRINOVICS, Edvards; (15 pag.)WO2017/39425; (2017); A1;,
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Related Products of 14542-71-3, A common heterocyclic compound, 14542-71-3, name is 3,5-Dibromo-4-methylanisole, molecular formula is C8H8Br2O, 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.

Stage 2-9 – Intermediate A1 in Scheme 1 was synthesised in eight steps using processes described in patent WO 02/058695 ;

The synthetic route of 14542-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/53158; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, belongs to ethers-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 60876-70-2, HPLC of Formula: C10H13BrO

[3-(4-Benzyloxy)phenoxy]benzo[b]thiophene-2-boronic acid was reacted with 4-(-tertbutoxy)bromobenzene according to the conditions described above for ?2-iodo-3-(4-benzyloxy)[phenoxy]-benzo[b]thiophene and 4-(tertbutoxy)phenyl boronic acid to give [2-(4-tertbutyloxyphenyl)-3-(4-benzyloxy)phenoxy]benzo[b] thiophene in 81% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(tert-butoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US5856339; (1999); A;,
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Reference of 589-10-6, 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. 589-10-6, name is (2-Bromoethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 110 N’-[1-imadazol-1-yl-1-[1-(2-phenoxyethyl)imidazol-2-yl]methylidene]-N,N-dimethylhydrazine (compound Nos. 111, 112) To a solution of ethyl imidazole-2-carboxylate (0.505 g, 3.60 mmol) in N,N-dimethylformamide (6 ml) were added beta-bromophenetole (0.804 g, 4.00 mmol) and potassium carbonate (0.598 g, 4.32 mmol), and the mixture was stirred at 80C for 1 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give ethyl 1-(2-phenoxyethyl)imidazole-2-carboxylate (0.869 g, 3.34 mmol, yield 93%).

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-Bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; EP2168951; (2010); A1;,
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Reference of 261762-35-0, 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. 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-benzyloxy-5,6,7,8-tetrahydro-1,6-naphthyridine (500 mg, 2.4 mmol) and 5-bromo-1,2-difluoro-3-methoxy-benzene (696 mg, 3.1 mmol) in dioxane (10 mL) was added tBuONa (345.6 mg, 3.6 mmol), Pd2(dba)3 (44 mg, 0.05 mmol) and RuPhos (34 mg, 0.07 mmol)under N2. After being heated with stuffing at 100 C for 12 hrs, the resulting mixture was filtered and concentrated in vacuo. The residue was purified to give 2-benzyloxy-6-(3,4-difluoro-5- methoxy-phenyl)-7,8-dihydro-5H-1,6-naphthyridine (500 mg), which was used in the next step without further purification.

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-1,2-difluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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Application of 29578-83-4,Some common heterocyclic compound, 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, molecular formula is C8H9BrO, 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 1 Synthesis of (1R,10R,11S,16S)-5-methoxy-1,3,11,15,15-pentamethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene Cu(I)I (0.05 g, 0.25 mmol) and NaI (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 min. Anhydrous dioxane (5 mL), N,N’-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and 1-bromo-3-methoxy-5-methylbenzene (1) (1.0 g, 5.0 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110 C. in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2Cl2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (2) (1.05 g, 87% yield) as a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-methoxy-5-methylbenzene, its application will become more common.

Reference:
Patent; Aquinox Pharmaceuticals Inc.; US2011/136802; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, belongs to ethers-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 89521-55-1, Recommanded Product: 89521-55-1

107C. 3:1 regio isomeric mixture of tert-butyl 4-(2-amino-3- (benzyloxy)phenylcarbamo vD- 1 -( 1 H-pyrazo Io [3 ,4-d1pyrimidin-4- yl)piperidin-4- ylcarbamate and tert-butyl 4-(2-amino-6-(benzyloxy)phenylcarbamoyl)-l-(lH- pyrazolor3,4-dlpyrimidin-4-yl)piperidin-4-ylcarbamate.N,N-Diisopropylethylamine (6.58 mL, 37.75 mmol) was added in one portion to a stirred suspension o f 4-(tert-butoxycarbonylamino)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4- yl)piperidine-4-carboxylic acid (9.12 g, 25.17 mmol) and O-(7-Azabenzotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (10.53 g, 27.68 mmol) in NMP (60 mL). The mixture was warmed to 5O0C for 15 minutes under nitrogen and cooled to 2O0C. 3-(benzyloxy)benzene-l,2-diamine (5.39 g, 25.17 mmol) was added in one portion and the resulting solution was stirred at 20 0C for 70 hours. The reaction mixture was diluted with EtOAc (200 mL), and washed sequentially with water (3 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product which was purified by flash silica chromatography, elution gradient 1 to 10% MeOH in DCM. Fractions containing product were were evaporated to dryness to afford a pink foam which was shown to be an 82% pure 3:1 regio isomeric mixture of tert- butyl 4-(2-amino-3 -(benzyloxy)phenylcarbamoyl)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4- yl)piperidin-4-ylcarbamate and tert-butyl 4-(2-amino-6-(benzyloxy)phenylcarbamoyl)-l- (lH-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-ylcarbamate. (8.1g, 58% of 82% pure), m/z (ESI+) (M+H)+ = 559; HPLC tR = 2.21 min (28%), 2.41 min (72%); IH NMR (399.9 MHz, DMSO-d6) delta 1.44 (9H, d), 1.96 (0.5H, m), 2.13 (1.5H, s), 3.72 (2H, d), 4.31 (IH, m), 4.46 (IH, m), 4.94 (0.5H, s), 5.13 (1.5H, s), 6.28 (0.25H, d), 6.32 (0.25H, d), 6.51 (0.75H, t), 6.62 (0.75H, s), 6.81 (0.75H, d), 6.90 (0.25H, m), 7.22 – 7.43 (6H, m), 7.50 (1.5H, d), 8.15 (0.25H, s), 8.25 (IH, m), 8.32 (0.75H, s), 8.61 (0.25H, s), 9.10 (0.75H, s), 13.51 (IH, s)

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-(Benzyloxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75109; (2008); A1;,
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Reference of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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.

At 5 C., a solution of bromine (9.8 mL, 192.5 mmol, 1.1 eq) in dichloromethane (120 mL) was added slowly to a dichloromethane solution (240 mL) of 4-bromo-2-methoxyaniline (35.35 g, 175 mmol) under vigorous stirring. The reaction mixture was kept at this temperature for 2 h. After the completion monitored by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3*200 mL). The organic layer was combined, washed with brine (3*50 mL) and dried over sodium sulfate. Then the reaction mixture was purified by flash column chromatography (ethyl acetate/hexanes (v/v)=5/95). The product (40.3 g, yield=82%) was obtained as a red liquid. 1H NMR (600 MHz, CDCl3) delta 7.20 (d, J=1.9 Hz, 1H), 6.84 (d, J=1.8 Hz, 1H), 4.21 (s, 2H), 3.86 (s, 3H). LRMS m/z 280.0 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Cierpicki, Tomasz; Grembecka, Jolanta; Huang, Huang; Zari, Sergi; Cho, Hyo Je; Potopnyk, Mykhaylo; Dudkin, Sergeii; Chen, Wenbing; Adam, Yassir; Howard, Christina; Kim, EunGi; US2019/183865; (2019); A1;,
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Synthetic Route of 175278-09-8,Some common heterocyclic compound, 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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: Triphosgene (0.14 g, 0.48 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.3 g, 1.2 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.2 mL, 1.44 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.2 mL, 1.44 mmol), 4-pyridin-3-ylaniline (5) (0.2 g, 1.2 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 6:1) yielding (L1). yield 73%

The synthetic route of 175278-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
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