Tag: M.W=100-200

Electric Literature of 17715-70-7,Some common heterocyclic compound, 17715-70-7, name is 2,4-Dimethoxy-1-fluorobenzene, molecular formula is C8H9FO2, 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.

Preparation 29 6-Fluoro-7-hydroxychroman-4-one A mixture of 1,3-dimethoxybenzene (3.80 mL, 29.0 mmol) and N-fluorodibenzenesulfonamide (4.21 g, 29.21 mmol) was heated at 60 C. overnight. The mixture was cooled and flash chromatographed on silica gel (2*5 inches packed in hexane) with elution proceeding as follows: 3% ethyl acetate/hexane (1000 mL), discarded forerun; 3% ethyl acetate/hexane (1000 mL), 2.69 g of a 2:1 mixture of 2,4-dimethoxyfluorobenzene and starting material which was carried directly into the next step. The product of the above reaction was combined with acetic acid (11 mL) and 48% HBr (11 mL) and refluxed 3 h. The reaction was concentrated and flash chromatographed on silica gel (2*5 inches packed in hexane) with elution proceeding as follows: 10% ethyl acetate/hexane (2000 mL), 0.95 g (43%) of 2,4-dihydroxyfluorobenzene as a waxy white solid which was used without purification. A mixture of 2,4-dihydroxyfluorobenzene (0.15 g, 1.17 mmol), 3-chloropropionic acid (0.13 g, 1.20 mmol) and trifluoromethanesulfonic acid (1 mL) were heated to 80 C. for 3 h. The reaction was poured into water and extracted with ether (3*). The combined organic phase was washed with water and brine, dried over magnesium sulfate, and concentrated to give 2,4-dihydroxy-5-fluoro-beta-chloropropiophenone as a red solid which had: NMR delta 7.37 (d, J=10.8 Hz, 1 H), 6.54 (d, J=7.7 Hz, 1 H), 3.87 (t, J=6.8 Hz, 2 H) 3.33 (t, J=6.8 Hz, 2 H). This product still contained some residual 3-chloropropionic acid but was suitable for use in the next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dimethoxy-1-fluorobenzene, its application will become more common.

Reference:
Patent; Pfizer Inc.; US6046213; (2000); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 17715-70-7 as follows. category: ethers-buliding-blocks

Example 15 Preparation of 4-fluororesorcinol (15) Using general method E, Compound 11 (27.4 g, 157.9 mmol) gives Compound 15 as 20.7 g (100%) of a colorless crystalline solid: m.p. 94-96 C.; 1 H-NMR (d6 -DMSO) 8.39 (br, 1H), 8.00 (br, 1H), 6.89 (dd, 1H), 6.48 (dd, 1H), 6.27 (ddd, 1H). 19 F-NMR (d6 -DMSO) 145.82 (m). Anal calc. for C6 H5 FO2: C, 56.26; H, 3.93. Found: C, 56.23; H, 3.93.

According to the analysis of related databases, 17715-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Molecular Probes, Inc.; US6162931; (2000); A;,
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. 53903-49-4, name is 4-Methoxy-2-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Formula: C8H8F3NO

2-Amino-5-methoxy-benzotrifluoride (10.46 mmol), K3PO4 (15.7 mmol), Xphos (1.05 mmol) and Pd4(dba)3 (0.314 mmol) were added under nitrogen to a solution of 4-bromo-2-fluoro-benzonitrile (10.46 mmol) in 50 mL toluene and the mixture was stirred for 20 hours at a bath temperature of 110 C. Then the mixture was filtered through a glass fibre filter, then the filtrate was extracted with 150 mL water. The organic phase was dried on sodium sulphate and evaporated down. In this way the product was obtained in a yield of 87% of theory. C15H10F4N2O (310.2) Mass spectrum (ESI): [M+H]+=311 [M-H]-=309 Thin layer chromatograph (silica gel; petroleum ether/ethyl acetate 7:3): Rf=0.48

The synthetic route of 53903-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/208823; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 4132-48-3, 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. 4132-48-3, name is 4-Isopropylanisole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 4 To each of two-separate 22-L three-necked, round-bottomed reaction flasks equally equipped with thermometer, reflux condenser and mechanical stirrer, there were charged 1.3 Kg (7.4 moles) of 4-isopropylanisole (the product of Example 2) and 12.0 L of trifluoroacetic acid at ambient temperatures (ca. 20 C.) with constant agitation being maintained throughout the course of the entire addition step. This was then followed by the slow addition of 1.0 Kg (7.4 moles) of hexamethylenetetramine in small portions over a 50-minute period to the two well-stirred reaction mixtures now contained in each of the two-separate reaction flasks. The resulting reaction mixture in each flask then exothermed from 24 C. to 38 C. in each instance and was thereafter externally heated up to the reflux temperature of the reaction mixture at 81 C. The stirred and heated reaction mixture was next refluxed at this point for a period of 14 hours. Upon completion of this step, the trifluoroacetic acid solvent was removed from each of the two spent reaction mixtures via concentration under reduced pressure and each resulting residual oil was thereafter partitioned between 4 L of water and 4 L of hexanes. The pH of the two-phase system now contained in each flask was subsequently re-adjusted from a pH value of 0.5 to a value of pH 9.0 by adding thereto separate-3.8 L and 4.2 L portions of 6N aqueous sodium hydroxide solution, respectively. The basified two-phase systems were then allowed to settle and separate, and the two-separated aqueous layers were thereafter saved and subsequently washed with a fresh 2 L-portion of hexanes. The organic layers were next combined and subsequently backwashed with 3 L of water, followed by treatment with 200 g of activated charcoal and 400 g of anhydrous magnesium sulfate as drying agent. After removal of the latter two substances by means of suction filtration through celite, the resulting clear organic filtrate was subsequently concentrated in vacuo to give 2.0 Kg (72%) of crude aldehyde final product in the form of a dark residual oil. The latter material (1.8 Kg) was then purified by means of distillation in vacuo to ultimately afford 880 g (44%) of pure 2-methoxy-5-isopropylbenzaldehyde. The pure product was characterized by means of nuclear magnetic resonance (NMR) data. NMR Data: 1 H NMR(CD3 OD) delta1.05(d, 6H), 2.74(m, 1H), 3.75(s, 3H), 6.95(d, 1H), 7.35(dd, 1H), 7.35(dd, 1H), 7.5 1H, 10.23(s, 1H).

The chemical industry reduces the impact on the environment during synthesis 4-Isopropylanisole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US5294744; (1994); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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: A corresponding primary amine (1.1 equiv.) and an excess of 37% formalinaldehyde free of paraformaldehyde (1.0 mL, 13.5 mmol) were added to a suspension of Guareschi imide triethylammonium salt 1a-c (0.8-0.9 mmol) in EtOH (6-12 mL). The mixture was refluxed for 3-5 min with stirring and allowed to stand for48 h at 20 C (precipitation of the corresponding “bispidinate”5a-m is possible). The mixture was acidified with 10% aqueousHCl to pH 3-4, after 1 day a precipitate formed was collected by filtration, washed with cold EtOH and diethyl ether, and, if necessary, recrystallized from the acetone-EtOH solvent system

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

Reference:
Article; Chigorina; Frolov; Dotsenko; Goloveshkin; Bushmarinov; Krivokolysko; Russian Chemical Bulletin; vol. 65; 9; (2016); p. 2260 – 2269; Izv. Akad. Nauk, Ser. Khim.; 9; (2016); p. 2260 – 2269,10;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 41566-77-2, A common heterocyclic compound, 41566-77-2, name is 5-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride, molecular formula is C10H14ClNO, 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.

To the solution of 5-methoxy-indan-1-ylamine hydrochloride (92 mg, 0.46 mmol) and (3- cyclopropyl-1 ,4-dimethyl-1 H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (buildingblock A7, 120 mg, 0.46 mmol) in DMF (6 ml) were added DIPEA (0.24 ml, 1.38 mmol) and HATU (210 mg, 0.55 mmol) and the reaction was stirred at rt for 30 min. The mixture was diluted with EtOAc, washed with aqueous bicarbonate solution and brine, dried over sodium sulfate, and the solvents were evaporated under reduced pressure. Purification by preparative HPLC (Gilson GX-281 , Waters Sunfire C18, 5muetaeta, 30 x 100 mm with guard column 19 x 10 mm, solvent A: water with 0.1% TFA, solvent B: acetonitrile, gradient 40-60% B in 15 min, flow reate 50 ml/min) gave the title compound as colorless solid (140 mg, 75%). [1 H-NMR (DMSO-de, 600 MHz) delta 8.40 (d, 1 H), 7.02 (d, 1 H), 6.81 (s, 1 H), 6.68 (d, 1 H), 6.48 (s, 1 H), 5.26 (dd, 1 H), 4.80 (s, 2H), 3.76 (s, 3H), 3.71 (s, 3H), 2.91-2.88 (m, 1 H), 2.78-2.73 (m, 1 H), 2.66 (s, 3H), 2.38-2.33 (m, 1 H), 2.28-2.24 (m, 1 H), 1.89-1.82 (m, 1 H), 0.92-0.85 (m, 4H); LCMS RtH = 3.095 min; [M+H]+ = 407.2]

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; BADIGER, Sangamesch; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; CHEBROLU, Murali; COSTESTA, Simona; HINTERMANN, Samuel; MEYER, Arndt; PANDIT, Chetan; WO2011/76744; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 4342-43-2,Some common heterocyclic compound, 4342-43-2, name is 2-Methoxycyclohexanamine, molecular formula is C7H15NO, 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 64 To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10-20 C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatograpy (Wakogel C-200, eluding solvent, benzene_chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. Elementary analysis for C13 H23 N5 O2 S: Calcd. (%): C,52.50; H,7.79; N,23.55 Found (%): C,52.56; H,7.71; N,23.63

The synthetic route of 4342-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Company, Limited; US4540703; (1985); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 2106-18-5, These common heterocyclic compound, 2106-18-5, name is 2-(Trifluoromethoxy)fluorobenzene, 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 20: 4-[2-FLUORO-3-(TRIFLUOROMETHOXY)PHENYL]-1-PROPYLPIPERIDIN-4-OL To a solution of 1-fluoro-2-(trifluoromethoxy)benzene (1.22 g, 6.77 mmol) in dry tetrahydrofurane (30 ml) at-78 C, under nitrogen, lithium diisopropylamide (2.5 M in hexane, 3.0 ml, 7.45 mmol) was added dropwise. The mixture was stirred for 1 h after which a solution of newly distilled 4-propyl-1-piperidone (0.96 g, 6.77 mmol) in dry tetrahydrofuran (20 ml) was added drop wise. The resulting mixture was stirred at-78 C for 30 min and then brought to ambient temperature. Water (100 ml) was added and the mixture was extracted with ethylacetate (3×100 ml). The combined organic phases was dried (MgS04), filtered and evaporated to dryness. The oily residue was purified by flash column chromatography (ethylacetate/methanol, 1: 1) to give the title compound (0.83 g). MS m/z (rel. intensity, 70 eV) 321 (M+, 5), 293 (14), 292 (bp), 274 (25), 207 (10).

Statistics shows that 2-(Trifluoromethoxy)fluorobenzene is playing an increasingly important role. we look forward to future research findings about 2106-18-5.

Synthetic Route of 151414-47-0, 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. 151414-47-0, name is 2,6-Difluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-Bromo-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazole (i.e. the product of Step B) (0.20 g, 0.66 mmol), palladium(II) acetate (15 mg, 0.066 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (76 mg, 0.13 mmol) and powdered potassium carbonate (1.8 g, 13 mmol) were combined in anhydrous 1,4-dioxane (3 mL), and the mixture was sparged with a subsurface stream of N2 gas for 10 min. 2,6-Difluoro- 4-methoxyaniline (0.22 g, 1.3 mmol) was added in one portion, and the reaction mixture was heated at reflux for 22 h. The reaction mixture was filtered through Celite diatomaceous filter aid, and the filter pad was washed with ethyl acetate (20 mL). The filtrate was washed with water (10 mL) and brine (10 mL), dried over MgSOz}, and concentrated to leave a semisolid residue. This residue was purified by column chromatography through 5 g of silica gel eluted with a gradient of hexanes/ethyl acetate (20: 1 to 1 :3) to give the title compound as a light-brown solid (48 mg).lU NMR delta 7.0-7.1 (m, 2H), 6.85 (m, 1H), 6.26 (m, 2H), 4.84 (br s, 1H), 3.78 (s, 3H), 3.66 (s, 3H), 2.08 (s, 3H). MS: 382 amu (AP+).

The synthetic route of 2,6-Difluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Electric Literature of 399-54-2, 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. 399-54-2 name is 4-Fluoro-1-methoxy-2-methylbenzene, 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.

Example 5 (not according to the invention) 56 g of 2-methyl-4-fluoro-methoxy-benzene were introduced into 150 ml of dichloromethane at 10 C. and 85 g of nitrating acid (HNO3 content 33%) were added dropwise in 30 minutes. The mixture was then stirred for 1 hour at 10 C. and 1 hour at 20 C. The reaction mixture was subsequently poured onto ice, extracted using dichloromethane, and the organic phase was separated off and distilled. The product passing over at 130 to 132 C. at 20 mbar was collected and filtered off with suction after stirring with 50 ml of n-hexane. 26 g of 2-methyl-3-nitro-4-fluoro-methoxy-benzene having a melting point of 38 to 40 C. were obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-1-methoxy-2-methylbenzene, and friends who are interested can also refer to it.