Month: March 2021

Synthetic Route of 53087-13-1, The chemical industry reduces the impact on the environment during synthesis 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, I believe this compound will play a more active role in future production and life.

General procedure: Under a nitrogen gas atmosphere, 3-bromoanisole(35 mL, 277 mmol) was added dropwise to a mixtureof magnesium (7.1 g, 292 mmol) and a catalytic amount ofiodine in tetrahydrofuran (THF) (270 mL), and the mixturewas stirred for 2 h. This reaction solution was added dropwiseto a solution of tert-butyl (2S)-2-{[methoxy(methyl) amino]-carbonyl}piperidine-1-carboxylate (8, 50.0 g, 184 mmol) inTHF (300 mL) under ice cooling, and the mixture was stirredat room temperature for 2 h. Ten percent aqueous NH4Cl solutionwas added, followed by extraction with EtOAc. Theorganic layer was washed with water and brine, dried overanhydrous Na2SO4, filtered, and concentrated in vacuo. Theresidue was purified using silica gel column chromatography(11% EtOAc in hexane) to yield 9c (32.7 g, 56%) as a pale yellowoil.

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-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yamamoto, Shuji; Shibata, Tsuyoshi; Abe, Kumi; Oda, Koji; Aoki, Takeshi; Kawakita, Yasunori; Kawamoto, Hiroshi; Chemical and Pharmaceutical Bulletin; vol. 64; 9; (2016); p. 1321 – 1337;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 104197-14-0, 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. 104197-14-0, name is 4-Bromo-2,6-difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 14. 2-r3,5-difluoro-4-(methyloxy)phenylH,4,5,5-tetramethyl-1.3,2- dioxaborolane; A solution of 4-bromo-2,6-difluoroanisole (223mg, 1 mmole), bis(pinacaolato)diboron (275 mg, 1.09 mmole), [1 ,1 ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (40 mg) and KOAc (300 mg) in 5 ml of dioxane was heated in the microwave at 150 for 20 minutes. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and evaporated. The residue was chromatographed on a Florisil column, and the titled compound was eluted with Et20, 158 mg (58%). 1H NMR (400 MHz, CDCI3) delta 7.32 (d, J=8Hz, 2H), 4.05 (s, 3H), 1.35 (s, 12H).

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-2,6-difluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 944317-92-4,Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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.

Argon gas is continuously fed into a 2L three-neck flask equipped with a mechanical stirrer, a Y-shaped tube, and a thermometer.10-0.9 g of 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene, 324 mL of tetrahydrofuran, 324 mL of toluene, and 130 mL of triisopropyl borate. The system was cooled down to -80 to -70C, and 253 mL of 2mol/L n-butyllithium was added dropwise to the system. The temperature drop was -80 to -70C. The addition was completed.After the incubation -80 ~ -70 C reaction 3h.The reaction solution was slowly poured into 1000 mL of dilute hydrochloric acid with a concentration of 1.2 M, and methyl tert-butyl ether (300 mL) was added. After stirring for 10 min, the mixture was allowed to stand for 5 min, and the aqueous phase was extracted with 500 mL of methyl tert-butyl ether. 10 min, stand for 5 min, and combine the organic phases. Add 1.0 L of 1M aqueous sodium hydroxide solution while stirring the organic phase, stirring10min, let stand 5min liquid.The organic phase obtained by liquid separation was further added with 300 mL of aqueous sodium hydroxide solution, stirred for 10 minutes, and allowed to stand for 5 minutes to separate liquids, and the organic phase was temporarily stored.Combine the aqueous phase, temperature control 0 ~ 15 C, with concentrated hydrochloric acid about 160mL adjust the system to pH = 1 ~ 2, temperature 0 ~ 15 C stirring 0.5h, filtration, filter cake rinse with water, bake to constant weight to give a white solid 4-(4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acid, 71.63 g (yield of 82.71%,4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acidLC = 99.68%,

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-4-fluoro-5-isopropyl-2-methoxybenzene, its application will become more common.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Yan Longjia; Yu Xinmin; Wang Xiaoming; Wang Xiaowei; He Hanjiang; (9 pag.)CN107365324; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 18800-30-1, These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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.

Example IX b) 52.0 g (186 mmol) of 1-bromo-4-(2-bromoethoxy)benzene is added to 300 mL THF and cooled down to 0 C. Within 30 min 25.0 g (223 mmol) KOtBu are added to this mixture in several portions. Cooling is removed and the reaction mixture is stirred at r.t. over night. The reaction is quenched by the addition of water. The resulting mixture is extracted with EtOAc (2¡Á). The org. phases are combined, washed with sat. aq. NaCl solution, dried with MgSO4, filtered and the solvent is removed in vacuo. The resulting product is used without further purification.

Statistics shows that 1-Bromo-4-(2-bromoethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 18800-30-1.

Reference:
Patent; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald Juergen; US2013/172316; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 126-38-5,Some common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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 solution of 3j (0.360?g, 2.00?mmol) and 1-bromo-2,4-dimethoxypropane (11, 0.330?mL, 2.44?mmol) in acetic acid (4.0?mL) was stirred at reflux for 3?h. After the solution was cooled to room temperature and concentrated, it was diluted with EtOAc and washed with water and saturated NaHCO3(aq). The organic layer was dried over MgSO4(s), filtered, and concentrated to afford a residue, which was purified by Isco Combi-Flash Companion column chromatography (0-20% EtOAc in n-hexane) to give 12 (0.114?g, 26%) as a yellow solid. 1H NMR (CDCl3, 300?MHz) delta 7.57 (d, 1H), 7.27-7.20 (m, 2H), 7.11 (dd, 1H), 7.05 (br s, 1H), 6.13 (s, 1H), 2.66 (q, 2H), 2.28 (s, 3H), 1.23 (t, 3H); 13C NMR (CDCl3, 75?MHz) delta 167.32, 148.57, 138.25, 136.07, 129.23, 127.04, 125.08, 121.85, 101.53, 24.32, 17.23, 14.25; HPLC Purity?=?100%, tR?=?29.20?min; LC-MS (ESI) m/z: 219.0 [M + H]+; HRMS (ESI): m/z calculated for C12H15N2S [M + H]+: 219.0956 Found: 219.0950.

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-2,2-dimethoxypropane, its application will become more common.

Reference:
Article; Lin, Shu-Yu; Kuo, Yu-Hsien; Tien, Ya-Wen; Ke, Yi-Yu; Chang, Wan-Ting; Chang, Hsiao-Fu; Ou, Li-Chin; Law, Ping-Yee; Xi, Jing-Hua; Tao, Pao-Luh; Loh, Horace H.; Chao, Yu-Sheng; Shih, Chuan; Chen, Chiung-Tong; Yeh, Shiu-Hwa; Ueng, Shau-Hua; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 312 – 323;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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. category: ethers-buliding-blocks

3,3-diethoxypropan-1-amine (6 g, 40.76 mmol, 1.00 equiv) was dissolved in 1,4- dioxane (30 mL) in the presence of TEA (4.45 g, 43.98 mmol, 1.08 equiv), then cooled to0C. (Boc)20 (9.6 g, 43.99 mmol, 1.08 equiv) diluted in 20 mL of 1,4-dioxane was added drop-wise. The solution was agitated 2 hours at 0C then overnight at ambient temperature before being neutralised with 10 mL of water. The pH was adjusted to 5 with HC1 (1 %). The solution was extracted 3 times with 50 mL of EtOAc. The organic phases were combined, dried over sodium sulfate, filtered and concentrated to yield 8.21 g (81 %) of compound 1ZDin the form of 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 41365-75-7, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; JOUHANNEAUD, Alexandra; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; CHAMPION, Thierry; ROBERT, Alain; HAEUW, Jean-Francois; RILATT, Ian; PEREZ, Michel; (244 pag.)WO2017/72196; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. HPLC of Formula: C11H25NO2

Step (2): synthesis of 4-formyl-benzoic acid tert-butyl ester:; 4-Formylbenzoic acid was suspended in 60 mL of benzene, and the mixture was placed under a nitrogen atmosphere. The mixture was brought to reflux and N,N -dimethylformamide di-tert-butylacetal was added dropwise via an addition funnel over 45 minutes. The yellowish suspension gradually turned golden yellow and became a homogeneous solution. The solution was refluxed an additional 60 minutes before stirring overnight at room temperature. The resulting orange solution was diluted to about 100 mL with ethyl acetate (“EtOAc”), and the resulting solution was washed sequentially with water, saturated sodium bicarbonate (2 x 100 mL), and brine (100 mL). The solvent was removed by rotary evaporation. The resulting amber oil was injected on to a BIOTAGE Flash 65i (350 g, silica gel) cartridge and purified with a 30-minute gradient of from 5% to 25% v/v EtOAc in heptane. Product fractions were pooled, and the solvent was rotary evaporated. The resulting golden oil was dried under house high vacuum overnight at room temperature to give 3.92 g (57% yield) of 4- formyl-benzoic acid tert-butyl ester as a yellow solid; IH NMR (400 MHz, DMSO-D6) delta ppm 1.54 (s, 9 H) 8.00 (dm, /=8.30, Hz, 2 H) 8.07 (dm, /=8.30, 2 H) 10.08 (s, 1 H); Mass Spectrum MH” 206.

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/61715; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-(difluoromethoxy)benzene

Example 178 2-[5-[4-(Difluoromethoxy)phenyl]-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide To a solution of the compound synthesised in Reference Example 36 (50.0 mg, 122 mumol), 1-bromo-4-(difluoromethoxy)benzene (20.1 muL, 147 mumol) and tetrakistriphenylphosphine palladium (7.08 mg, 6.12 mumol) in 1,4-dioxane (2.0 mL) is added a solution of potassium carbonate (50.8 mg, 367 mumol) in water (0.40 mL), and the mixture is stirred under reflux for 2 hours. After the reaction, the reaction mixture is poured into water at 0C, and extracted with ethyl acetate. The organic layer is washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The drying agent is removed by filtration, and the solvent is evaporated under reduced pressure. The obtained crude product is purified by silica gel chromatography (hexane/ethyl acetate = 3/1) to give 2-[5-[4-(difluoromethoxy)phenyl]-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide (21.1 mg, 41 %). IR (cm-1): 696, 1111, 1495, 1674, 1774

The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1719761; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C18H21NO4

General procedure: The corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 116557-46-1, 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. 116557-46-1, name is 3-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3 A solution of 3-bromo-2-methoxyaniline from Step 2 (1.94 g, 9.60 mmol), 4,4,445,5,55′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (3.66 g, 14.40 mmol), PdCl2(dppf)-CH2Cl2 complex (0.392 g, 0.480 mmol) and potassium acetate (2.83 g, 28.8 mmol) in dioxane (32 mL) in a flask was heated to reflux (-100 C) overnight then cooled to room temperature, concentrated in vacuo on CELITE. This crude product was purified by flash chromatography using a 120g silica gel column (solid loading) eluting with 0-50% ethyl acetate/hexanes. Appropriate fractions (eluted near 25% EtOAc/hexanes) were collected and concentrated in vacuo to give 2-methoxy-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.47 g, 5.78 mmol, 60.2% yield) as a crystalline off-white solid. LCMS MH+ 250.1.

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-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem