Category: 22094-18-4

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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,3-Dibromo-2,2-dimethoxypropane

A suspension of sodium hydride (2 g, 50.0 mmol) in DMF (20 ml) was cooled to 0 degree before 2-(4-bromophenyl)acetonithle (4 g, 20.40 mmol) was added slowly. The suspension was stirred at 0 degree for another 10min before 1,3-dibromo-2,2- dimethoxypropane (2.62 g, 10.00 mmol) was added. The reaction mixture was stirred at60 C for 20h before cooled to room temperature, poured into water (75ml) and extracted with ethyl acetate (2X50ml). The combined organic phase was washed with water (75ml), brine (50ml) and concentrated. The crude product was purified by column (100g, biotage) eluted with ethyl acetate/cyclohexane (0-10%) to afford product 1.7g (59% yield). NMR (500 MHz, DMSO-d6): 7.46 (d, 2H), 7.29 (d, 2H), 3.21 (s, 3H), 3.11 (s, 3H), 3.03 (d, 2H), 2.62 (d, 2H).

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 22094-18-4.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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. name: 1,3-Dibromo-2,2-dimethoxypropane

To a suspension of NaH (4.1 g, 100 mmol) (60% in mineral oil) in DMF (100 mL) was added 2-(4-bromophenyl)acetonitrile (10 g, 51 mmol) followed by l,3-dibromo-2,2-dimethoxypropane (11 g, 42 mmol). The reaction mixture was heated to 60 C for 12 h. After 12 h the reaction mixture was diluted with water (1000 mL) and washed with EtOAc (400 mLx2). The combined organics were washed with brine (100 mL), dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica (petroleum ether : EtOAc = 50: 1 to 20: 1) to afford 1-(4-bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile. MS (ESI) Calc’d [M+H]+, 296; found, 296.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22094-18-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; SCIAMMETTA, Nunzio; WHITE, Catherine, M.; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (109 pag.)WO2019/74747; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22094-18-4, A common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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 129A 3,3-dimethoxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarboxamide 2-[4-(Trifluoromethoxy)phenyl]acetonitrile (7.86 mL, 50 mmol), 1,3-dibromo-2,2-dimethoxypropane (13.10 g, 50.0 mmol), and sodium tert-butoxide (10.57 g, 110 mmol) were dissolved in DMSO (100 mL) and water (5 mL), and the mixture was heated for 1 hour at 125 C. The reaction was cooled to ambient temperature and stirred overnight. The reaction mixture was diluted with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgSO4, filtered, and concentrated to give the title compound (17.02 g, 53.3 mmol, 107% yield). MS (DCI+): m/z 320.1 (M+H), 337.1 (M+NH4). 1FINMR (300 MHz, DMSO-d6) delta 7.44 (d, J=8.8 Hz, 2H), 7.34 (s, 1H), 7.31 (d, J=8.8 Hz, 2H), 6.90 (s, 1H), 3.05 (s, 3H), 3.02-2.93 (m, 5H), 2.41 (d, J=13.4 Hz, 2H).

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2014/80803; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

To a suspension of NaH (120 g , 3.0 mol) in DMF (1 L) was added dropwise diisopropyl malonate (507 g, 2.7 mol) under an Ar atmosphere, and the reactionwas stirred.Compound 29.2(360 g, 1.35 mol) was then added in portionsand the mixturewas heated to reflux for 48 hr.The reaction mixture was poured into water (2 L), and extracted with PE (6 x 1 L). The combinedorganic layers were dried, filteredand concentrated under reduced pressure 15 to give a yellow oil, which was purified by distillation under reduced pressureto yield compound 29.3 (150 g, 45%) as a colorless oil.

According to the analysis of related databases, 22094-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHAOGEN, INC.; LINSELL, Martin Sheringham; AGGEN, James Bradley; DOZZO, Paola; HILDEBRANDT, Darin James; COHEN, Frederick; KASAR, Ramesh Annasaheb; KANE, Timothy Robert; GLIEDT, Micah James; MCENROE, Glenn A.; WO2014/165075; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 22094-18-4, 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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

Under a nitrogen atmosphere, a 5L three-neck flask was charged with a starting material, ethanesulfonamide (163.5 g, 1.5 mol).Anhydrous potassium carbonate (275.8g, 2.0mol) and anhydrous DMF (1L) were stirred for 30min.Then 1,3-dibromo-2,2-dimethoxypropane (SM) (259.9 g, 1.0 mol) was added,Stir for 30 min, then raise the temperature of the reaction system to 95-100 C.20-22 hours at this temperature,Then cool to room temperature.After that, the pH was adjusted to 2 to 3 with 0.1N HCl, and the mixture was stirred well for 2-3 hours. Then, 2L of water was added to the system to precipitate a lot of off-white solid, which was filtered and dried to obtain 134.1 g of a solid. The yield was 82.3. %.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2,2-dimethoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Xiamen Hailejing Biochemical Co., Ltd.; Zhong Baoxiang; Qiu Binglin; Chen Huadong; Li Jinlin; Huang Zhizheng; (9 pag.)CN107739328; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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. COA of Formula: C5H10Br2O2

Reference Example 2; Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylateTo DMF solution (1.8 L) comprising diisopropyl malonate (1437 g), sodium hydride (367 g) was added at 15 C. Subsequently, 1,3-dibromoacetone dimethylacetal obtained from Reference example 1 was added thereto, stirred at 130 C. for 24 hours, followed by further stirring for three days. Upon the completion of stirring, the reaction was terminated by adding aqueous solution of ammonium chloride, and extraction was carried out using hexane. The organic layer was washed with water, and then dried over magnesium sulfate. Solids were removed, and the filtrate was dried under reduced pressure. Thus obtained residues were subjected to flash column chromatography (using 10:1 (v/v) hexane/ethyl acetate as an eluent) to obtain the title compound (1.5 kg).1H-NMR (CDCl3): 5.08 (2H, m), 3.15 (6H, s), 2.69 (4H, s), 1.24 (12H, m).

The synthetic route of 1,3-Dibromo-2,2-dimethoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/298894; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22094-18-4, A common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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 114A 3,3-dimethoxy-1-(3-(trifluoromethoxy)phenyl)cyclobutanecarboxamide The mixture of 1,3-dibromo-2,2-dimethoxypropane (1310 mg, 5.00 mmol), sodium tert-butoxide (1057 mg, 11 mmol) and 2-(3-(trifluoromethoxy)phenyl)acetonitrile (1006 mg, 5 mmol) in DMSO (12 mL) was stirred at 25 C. for about 16 hours, then heated at about 125 C. for about 30 minutes. The solution was cooled to room temperature, diluted with water, and extracted with ether three times. The organic phase was washed with saturated NH4Cl. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude mixture was purified by silica gel chromatography (50% Hexanes/EtOAc to 100% EtOAc) to afford the product (450 mg, 28.2%). LC-MS: m/z (M+H) 288. 1H NMR (400 MHz, DMSO-d6): delta 7.44-7.48 (t, J=8 Hz, 1H), 7.41 (s, 1H), 7.34-7.36 (d, J=7.6 Hz, 1H), 7.30 (s, 1H), 7.22-7.24 (d, J=8 Hz, 1H), 6.95 (s, 1H), 3.05 (s, 3H), 3.00 (s, 3H), 3.00-2.95 (d, J=14 Hz, 2H), 2.43-2.40 (d, J=12.8 Hz, 2H).

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; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2014/80803; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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 22094-18-4, name: 1,3-Dibromo-2,2-dimethoxypropane

A suspension of NaH (110 g, 4580.1 mmol) in DMF (1.6 Lit) was cooled to 0 C, prior to the dropwise addition of 2-(3-fluorophenyl)acetonitrile (206 g, 1526.7 mmol) over 2 h. Reaction mixture was brought to rt and stirred for 45 min. To this mixture was added l,3-dibromo-2,2-dimethoxypropane (200 g, 763.3 mmol) in one portion at RT and stirring was continued at RT for 16 h, before heating at 80 C for 3 h. The reaction mixture was cooled to 0 C and quenched with crushed ice water (500 mL) and diluted with water (2.5 L), extracted with ethyl acetate (2×2 L). The combined organic layer was washed with brine solution (3×3 L), dried over Na2S04, filtered and the filtrate was concentrated. The crude compound was purified by silica gel column chromatography (100-200 mesh), eluting with 2-3% ethyl acetate in pet-ether to afford 114 g (63%) of l-(3- fluorophenyl)-3,3-dimethoxycyclobutanecarbonitrile (INT-27) as a colorless liquid (TLC system: 15%o ethyl acetate in pet ether; Rf: 0.4).

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, 1,3-Dibromo-2,2-dimethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; RATCLIFFE, Paul; KONETZKI, Ingo; SITNIKOV, Nikolay; KOCH, Thomas; JOSTOCK, Ruth; (121 pag.)WO2019/12037; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 22094-18-4, 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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

Diisopropyl malonate (72 g, 0.38 mol) was added dropwise, under nitrogen, to a stirred suspension of sodium hydride (17 g, 0.42 mol) in dry N,N-dimethylformamide (140 mL, 1.8 mol) at a rate such that the temperature was maintained below 70 C. On cessation of hydrogen evolution, 1,3-dibromo-2,2-dimethoxypropane (50 g, 0.2 mol) was added in one portion and the mixture heated at 140 C. for 48 h. The cooled mixture was poured into sat. solution of ammonium chloride (300 mL), extracted with hexane. The organic layer was washed with sat. sodium bicarbonate, brine, dried over sodium sulfate, and evaporated to dryness. The residue was distilled under vacuum (oil pump) to afford the desired cyclobutane compound (31 g, 56.32%). bp 92-94 C./0.01 mm). 1H NMR (400 MHz, CDCl3): delta 5.02 (2H, sept., J=6.4 Hz), 3.12 (6H, s), 2.66 (4H, s), 1.11 (12H, d, J=6.4 Hz.) ppm.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2,2-dimethoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; US2009/233903; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H10Br2O2

A suspension of sodium hydride (2 g, 50.0 mmol) in DMF (20 ml) was cooled to 0 degree before 2-(4-bromophenyl)acetonithle (4 g, 20.40 mmol) was added slowly. The suspension was stirred at 0 degree for another 10min before 1,3-dibromo-2,2- dimethoxypropane (2.62 g, 10.00 mmol) was added. The reaction mixture was stirred at60 C for 20h before cooled to room temperature, poured into water (75ml) and extracted with ethyl acetate (2X50ml). The combined organic phase was washed with water (75ml), brine (50ml) and concentrated. The crude product was purified by column (100g, biotage) eluted with ethyl acetate/cyclohexane (0-10%) to afford product 1.7g (59% yield). NMR (500 MHz, DMSO-d6): 7.46 (d, 2H), 7.29 (d, 2H), 3.21 (s, 3H), 3.11 (s, 3H), 3.03 (d, 2H), 2.62 (d, 2H).

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 22094-18-4.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem