Tag: M.W=200-300

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. 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, A new synthetic method of this compound is introduced below., SDS of cas: 29578-83-4

3-Bromo-5-methoxybenzoic acid To a vigorously stirred mixture of 1-Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMnO4 (3.14 g, 19.89 mmol) at 105 C. The mixture which turned to a black suspension was stirred 24 hours at 105 C., then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCl. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24% yield) as a white solid. MS: 229.1 [M+H]+, Rt(1)=1.18 min.

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; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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 53087-13-1, SDS of cas: 53087-13-1

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (1.29 g, 52.8 mmcl) in dry THF (50 mL). The mixture was refluxed and about 5% of a solution of 3- bromophenol (13.9 g, 52.8 mmcl) was added. When the reaction had started, the solution of thebromide was added drop-wise and the mixture was then refluxed for one more hour. The mixture was cooled down to about 5 C and a solution of the cyclopentanone (4.44 g, 52.8 mmcl) in THF (50 mL) was added drop-wise. The mixture was stirred at rt for 72 h, then the reactio was quenched with cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered andconcentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(Benzyloxy)-3-bromobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVIR AB; KALAYANOV, Genadiy; PINHO, Pedro; WESTERLIND, Hans; WIKTELIUS, Daniel; WAeHLING, Horst; WO2015/56213; (2015); A1;,
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Synthetic Route of 51388-20-6, These common heterocyclic compound, 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, 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 solution of 4-benzyloxyaniline hydrochloride (compound Ia, 12 g) in MeOH (200 mL) was treated with aqueous NaOH (2.04 g in 80 mL deionized water) and the resulting clear solution was concentrated to dryness to provide a residue of crude aniline free base.

The synthetic route of 51388-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2009/140553; (2009); A2;,
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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;,
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Application of 701-07-5, 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. 701-07-5 name is 2-(2′-Bromophenoxy)propane, 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.

Step 2: magnesium (350 mg, 14.42 mmol) was suspended in small amount of dry THF. Few crystals of iodine was added followed by 1 -bromo-2- isopropoxybenzene (1 g, 4.65 mmol) dissolved in dry THF. The reaction mixture was stirred at rt. The completion of halogen exchange was monitored by TLC. 2-Methyl-N-[(1 E)-(5-methylfuran-2-yl)methylidene]propane-2- sulfinamide (3.03 g, 13.95 mmol) diluted in dry THF was added dropwise at rt. The solution was stirred at rt for 2h. Sat. NH4CI was used to quench the reaction. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under vacuo. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (4:1 ) as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2′-Bromophenoxy)propane, and friends who are interested can also refer to it.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, 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 17715-69-4, Computed Properties of C8H9BrO2

General procedure: A solution of 4-methoxybromobenzene (2.67 mmol)and cyclopent-2-en-1-one (3.2 mmol) in DMSO was stirred at ambient temperaturefor 10 min under nitrogen, and treated with Na2CO3 (8.01mmol) and tri-tert-butylphosphonium tetrafluoroborate (0.53 mmol).The reaction mixture was degassed with nitrogen for 10 min and treated withPd(PPh3)2Cl2 (0.13 mmol) and X-Phos (0.26mol), and stirred at 100 0C for 12 h. The reaction mixture was cooledto ambient temperature, diluted with water, and extracted with AcOEt (3 x 50ml). The combined organic layers were washed with brine, dried over anhydrousNa2SO4, and evaporated. Flash chromatograph on silica gel(AcOEt:cyclohexane 1:3) provided the Heck coupling product as brown solid (340mg, 68percent).

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-Bromo-2,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gowala, Tarak Nath; Pabba, Jagadish; Tetrahedron Letters; vol. 56; 14; (2015); p. 1801 – 1804;,
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Application of 261762-35-0, A common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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.

Step 1: Preparation of 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8- azaspiro[4.5]decane To a mixture of 5-bromo-1,2-difluoro-3-methoxy-benzene (1.1 g, 4.93 mmol), 1,4-dioxa-8- azaspiro[4.5]decane (0.85 g, 5.92 mmol) and t-BuONa (0.95 g, 9.86 mmol) in 1,4-dioxane (10 mL) was added Pd2(dba)3 (92 mg, 0.10 mmol) and Ru-Phos (92 mg, 0.20 mmol) successively under N2. After being heated at 100 oC with stirring overnight, the reaction mixture was cooled down to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.57 g) which was used in the next step directly without further purification.

The synthetic route of 261762-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)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. Quality Control of 1-Bromo-4-(difluoromethoxy)benzene

Step 4) 1-difluoromethoxy-4-{3-[3-(2-methoxy-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-methoxy-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (1.00 g, 2.70 mmol) was dissolved in THF (5 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (5 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (1.20 gm, 5.38 mmol), copper iodide (70 mg, 0.262 mmol), tetrakis(triphenylphosphine)palladium (140 mg, 0.120 mmol) and triethylamine (5.8 g, 98 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%-10% EtOAc in hexanes) afforded an oil 882 mg (46%). This material was used in next step without further characterization.

The synthetic route of 1-Bromo-4-(difluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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.

Copper iodide (54 mg, 0.283 mmol) and Tetrakis(triphenylphosphine) palladium (105 mg, 0.091 mmol) were added. Lastly 1-bromo-4-(difluoromethoxy)benzene (0.750 g, 3.36 mmol) was added, the vial was covered with a teflon septa, an aluminum cap was crimped in place, and the assembly was set on a Biotage Emrys microwave instrument to irradiate at 80 C. for 30 minutes. The crude reaction was diluted with diethylether, washed with saturated ammonium chloride, and purified via column chromatography on a Yamazen W-Prep 2XY using 25% EtOAc in hexanes. Concentration by rotary evaporation afforded 500 mg of oil (96%); 1H NMR (400 MHz, DMSO-d6) delta ppm 3.03 (t, J=4.6 Hz, 4H) 3.73 (t, J=4.6 Hz, 4H) 7.13-7.14 (m, 1H) 7.16 (d, J=2.6 Hz, 1H) 7.17-7.19 (m, 2H) 7.22 (d, J=8.8 Hz, 2H) 7.24 (t, J=73.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H); MS (ES) m/z 348.2 [M+H]+

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-(difluoromethoxy)benzene, its application will become more common.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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

To the reaction vessel of 3000 L was added the above-obtained 2,3-difluoro-5-bromoanisole and 215 kg of AlCl3,And then pumped into 1800L of toluene,Sealed reactor, heated to reflux after 5h sampling analysis,Raw materials have been basically complete.The material with nitrogen into the 5000L washing kettle,Pumped into 1000L water stirring washing, discard the water layer,And then repeated washing once a few layers into the distillation kettle,After the toluene was distilled off, it was distilled under reduced pressure to obtain 206.1 kg of 2,3-difluoro-5-bromophenol,The product content of GC was 99.4%.The recovered toluene can be reused after drying. The total yield of the two-step reaction was 82.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 261762-35-0, its application will become more common.

Reference:
Patent; Zhejiang Linjiang Chemical Industry Co., Ltd.; Yi, Miao; Yin, Xin; Chen, Huanjun; Wang, Qijin; Xu, Xin; (8 pag.)CN106478377; (2017); A;,
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