Tag: M.W=200-300

Reference of 5111-65-9, 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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows.

SYNTHESIS EXAMPLE 1; According to a reaction path of Reaction Scheme 1, compound 19 represented by Formula 19 was synthesized: Synthesis of Compound 19; Synthesis of Intermediate A; 7.5 g (32 mmol) of 2-bromo-6-methoxynaphthalene, 4.6 g (25 mmol) of phenoxazine, 3.7 g (38 mmol) of sodium tert-butoxide ((t-BuO)Na), 0.3 g (0.33 mmol) of Pd2(dba)3 [(tris(dibenzylidine acetone) dipalladium (0))], and 0.11 g (0.55 mmol) of tri(tert-butyl)phosphine were dissolved in 125 mL of toluene and were reacted for 12 hours at 80 C.After the reaction was completed, the reaction mixture was cooled down to an ambient temperature and 200 ml of distilled water was added and quenched. Then, xylene and water were extracted in the volume ratio of 1:1.The collected organic layer was dried and concentrated using MgSO4 and a column chromatography was performed using an eluant formed of toluene and hexane in the volume ratio of 1:2. The obtained effluent was concentrated and dried to obtain 6.8 g (Yield: 80%) of intermediate A. The structure of intermediate A was identified through 1H NMR spectroscopy.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-6-methoxynaphthalene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Son, Jhun-Mo; Yu, Eun-Sun; Kwon, O-Hyun; Son, Young-Mok; Kim, Yu-Jin; US2007/176541; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 24988-36-1, 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. 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 14 is combined with anhydrous tetrahydrofuran:dioxane (5:0.9), and the mixture is agitated under a nitrogen atmosphere until a homogeneous solution is achieved. The solution is cooled to -3 C and 1.3 eq. of /-PrMgCl-LiCl in tetrahydrofuran is added. The reaction mixture is agitated at 0 C until the formation of the mono-Grignard is complete as determined by HPLC analysis. Next, a solution of 1.1 eq. of 3-chloro-2-fluorobenzaldehyde in tetrahydrofuran is added. This mixture is allowed to stir at 0 0C until the formation of Compound 15a is complete by HPLC. Next, additional /-PrMgCl-LiCl solution in tetrahydrofuran (2.5 eq.) is added and the reaction mixture is warmed to about 20 C. After conversion to the second Grignard intermediate is complete, the reaction mixture is cooled to 3 C. Anhydrous CO2 (g) is charged to the reaction mixture at about 5 0C. The reaction mixture is adjusted to about 20 C. After the carboxylation reaction is complete by HPLC, the reaction mixture is cooled to about 10 C and water is charged to quench the reaction followed by the addition of concentrated hydrochloric acid to adjust the pH to no more than 3. The reaction mixture is then warmed to about 20 C. The phases are separated. The organic phase is solvent exchanged to a mixture of isopropyl alcohol and water and the resulting slurry is cooled to about 0 0C. The product is isolated by filtration, washed with a mixture of isopropyl alcohol and water and dried at about 40 C to yield Compound 3.

The synthetic route of 1,5-Dibromo-2,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2009/36161; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Bromo-3-methoxyaniline (380 mg, 1.88 mmol), 2-(2-chlorophenylamino)-2-methylpropanoic acid (482 mg, 2.26 mmol) and diisopropylethylamine (413 mg, 558 jil, 3.2 mmol) were combined with dimethylformamide (15 ml). 0- (7 -Azabenzotriazol- 1 -yl)-N,N,N? ?N? – tetramethyluronium hexafluorophosphate (HATU, 1.22 g, 3.2 mmol) was added. The reaction mixture was stirred at room temperature oyernight. Reaction mixture was poured on water andextracted with dichloromethane. Chromatography (silicagel, ethyl acetate / heptane = 20:80 to50:50) yielded N-(4-bromo-3-methoxyphenyl)-2- (2-chlorophenylamino)-2-methylpropanamide (457 mg, 61percent) as brown solid. MS: mle =399.3 [M+H].

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-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECCARELLI, Simona M.; JAGASIA, Ravi; JAKOB-ROETNE, Roland; PETERS, Jens-Uwe; WICHMANN, Juergen; WO2014/79850; (2014); 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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

A solution of [2-(trifluoromethyl)phenyl]acetic acid (3.06 g, 15.0 mmol) in toluene (30 mL) was heated to 80C, 1,1-di-tert-butoxy-N,N-dimethylmethaneamine (14.4 g, 60.0 mmol) was added and the mixture was stirred at 80C for 2 hr. After cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The obtained extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100 – 30/70) to give tert-butyl [2-(trifluoromethyl)phenyl]acetate (3.16 g, 81%). To a solution of tert-butyl [2-(trifluoromethyl)phenyl]acetate (3.10 g, 11.9 mmol) in DMF (36 mL) was added sodium hydride (60% oil, 524 mg, 13.1 mmol), and the mixture was stirred at room temperature for 30 min. 1-Chloro-3-iodopropane (1.34 mL, 12.5 mmol) was added, and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100 – 30/70) to give tert-butyl 5-chloro-2-[2-(trifluoromethyl)phenyl]pentanoate (3.63 g, 91%). A solution of tert-butyl 5-chloro-2-[2-(trifluoromethyl)phenyl]pentanoate (3.56 g, 9.83 mmol) in TFA (10 mL) was stirred at room temperature for 18 hr. The solvent was evaporated under reduced pressure, ethyl acetate was added, and the mixture was extracted with 1 M aqueous sodium hydroxide solution. The extract was acidified with 6 M hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (2.74 g, 99%). 1H NMR (CDCl3) delta: 1.55 – 1.75 (1 H, m), 1.76 – 2.04 (2 H, m), 2.16 – 2.34 (1 H, m), 3.50 (2 H, t, J=6.3 Hz), 4.06 (1 H, t, J=7.3 Hz), 7.31 – 7.45 (1 H, m), 7.46 – 7.62 (2 H, m), 7.67 (1 H, d, J=7.7 Hz).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2455380; (2012); A1;,
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. 867288-00-4, name is 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine

A solution of 123 L of a 10% aqueous solution of Na2C03, 1.5 L of a 25 wt. % aqueous solution of ammonia and 2.0 kg of a filtration resin (Dicalite) were charged to the reactor and the mixture stirred for 5 minutes. The mixture was recirculated through a filter until clarification of the liquors (35 min) and charged into a reactor. 60 L of isopropyl acetate were added and the mixture was stirred for 10 minutes and the phases (A1 +01 ) were allowed to separate. The aqueous phase (A1 ) was transferred to a different reactor and 60 L of isopropyl acetate were charged. The mixture was stirred and the phases (A2 + 02) were allowed to separate. Both organic phases (01+02) were charged into a reactor and 108 L of a 10 wt. % aqueous solution of Na2C03 were added. The mixture was stirred and the phases (A3+03) were allowed to separate. The organic phase (03) was stirred with 108 L of a 10 wt. % aqueous solution of Na2C03 and the phases (A4+04) were allowed to separate. The organic phase (04) was stirred with 100 L demineralised water and the phases (A5+05) were allowed to separate. The organic phase (05) was filtered over a filtration resin (Dicalite) in a filter and charged in to a reactor. 2.2. Distillation: The organic phase (05) was distilled during 2 hours under reduced pressure (approx. 750 mm Hg) keeping the distilled mixture at temperature below 65 C.

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; ALMIRALL, S.A.; BOIX BERNARDINI, Maria, Carmen; WO2011/45059; (2011); 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. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C19H17NO

To a 250 mL four-necked flask was added a solution of 4-methoxytriphenylamine in DMF (previously prepared from 5.5 g of 4-methoxytriphenylamine dissolved in 75 mL of DMF), protected by nitrogen and magnetically stirred and cooled to 0 C. ,Using a constant pressure dropping funnel, 12.24g of POCl3 was slowly added dropwise to the reaction solution. After the addition was completed, the reaction conditions were maintained for 1h. Heating to 80 reaction.After the reaction was completed, the reaction mixture was poured into ice water and quenched, extracted with methylene chloride, washed with deionized water five times and anhydrous sulfurThe mixture was dried over magnesium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was separated by column chromatography (petroleum ether / ethyl acetate = 10/1, v / v)Pure, to obtain a green oily liquid, the yield was 94.8%.

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 4316-51-2.

Reference:
Patent; Hebei University of Science and Technology; Lv Haijun; Zhou Haoran; Jin Gengen; Yu Yifeng; Ma Weiqing; Kang Caihong; Wang Lili; (37 pag.)CN107298689; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 64115-88-4, These common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)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.

Into a 300-mi glass reaction vessel equipped with a stirring apparatus were placed 10.0 g (42 mmol) of 1-bromo-2-(trif- luoromethoxy)benzene, 2.9 g (4.2 mmol) of dichiorobis (triphenylphosphine)palladium(II), 20.1 g (54 mmol) of 2-(tributyltin)thiophene, and 100 ml of toluene. The mixture was reacted at an internal temperature of about 100 C. for 4 hours. After the completion of the reaction, the solvent was concentrated, and then 300 ml of hexane was added to the reaction solution. Subsequently, the mixture was filtered through [silica gel:potassium carbonate=90: 10 (wt %)]. The filtrate was concentrated, and the concentrate was purified bycolumn chromatography (hexane: 100 vol %), to provide 6.6 g of Compound (3-1) in the form of a pale yellow liquid.The properties of Compound (3-1) were as follows.?H-NMR (400 MHz; CDC13); 7.09-7.14 (m, 1H), 7.27- 7.37 (m, 3H), 7.37-7.41 (m, 1H), 7.41-7.44 (m, 1H), 7.63-7.70 (m, 1H)

The synthetic route of 64115-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; Tokito, Shizuo; Kumaki, Daisuke; Shima, Hidetaka; Oda, Hiroyuki; Tanaka, Yasuhiro; Kakita, Kazuaki; Machida, Toshikazu; Yoneda, Yasuhiro; Omata, Youji; Shimano, Tetsuro; (55 pag.)US9290516; (2016); B2;,
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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H5BrF3NO

EXAMPLE 122 N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-8-(trifluoromethoxy)-3-quinolinecarboxamide [] A mixture of 4-bromo-2-trifluoromethoxyaniline (10.0 g) and diethyl ethoxymethylenemalonate (7.9 mL) is heated to 135 C for 2 h. The reaction mixture is diluted with diphenylether (90 mL) and heated to reflux with removal of ethanol by a Dean-Start trap for 30 min. The resulting precipitate is poured into heptane and filtered to afford 10.83 g (73%) of the 6-bromo-8-trifluoromethoxyquinoline ethyl ester. A mixture of the quinoline ethyl ester (5.0 g) and 4-chlorobenzylamine (12.0 mL) are heated to 190 C for 1 h. The mixture is diluted with toluene (25 mL), allowed to cool to rt, and filtered. The crude product is recrystallized (HOAc, water) to afford 5.03 g (80%) of the amide. The resulting amide (469 mg), bis(triphenylphosphine)palladium (II) chloride (175 mg), and triethylamine (5.0 mL) are dissolved in DMF (50 mL). Propargyl alcohol (2.5 mL) is added over 20 h at 90 C. The reaction mixture was allowed to cool to rt, poured into aq. ammonium chloride (200 mL) and extracted with ethyl acetate (4 x 50 mL). The organic layer is washed with sat. aqueous brine (10 mL). The aqueous layer is back-extracted with ethyl acetate (20 mL). The combined organic layers are dried (MgSO4) and concentrated. The crude product is purified by column chromatography (dichloromethane/ methanol, 100/1; 50/1; 100/3) to afford 580 mg (26%) of the title compound as a white solid. Physical characteristics are as follows: Mp 262 C dec.1H NMR (DMSO-d6) delta 12.89, 10.12, 8.64, 8.20, 7.86, 7.42-7.34, 5.42, 4.55, 4.35.13C NMR (CF3CO2D) delta 175.7, 167.4, 144.1, 139.1, 134.8, 133.3, 131.5, 129.2, 129.1, 127.3, 126.3, 123.6, 123.2, 120.6, 107.3, 84.8, 84.1, 55.5, 44.1.IR (drift) 1936 (w), 1657 (s), 1602, 1574, 1544, 1517 (s), 1279 (s), 1268, 1223 (s), 1212 (s), 1183, 1161 (s), 1048, 1020, 802 cm-1.MS (ESI-) m/z 449 (M-H)-.Anal. Found for C21H14ClF3N2O4: C, 55.86; H, 3.16; N, 6.09; Cl, 7.96

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 175278-09-8.

Reference:
Patent; Pharmacia & Upjohn Company LLC; EP1042295; (2005); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, 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 4463-59-6, Safety of 1-(2-Bromoethoxy)-2-methoxybenzene

EXAMPLE 68 1-[2-(2-Methoxyphenoxy)ethyl]-4-benzamidopiperidine 2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heatedon a steam bath for 4 hr. The resulting mass was crushed and stirred in water (200 ml.) at 60 for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4. Analysis: Found C, 64.74; H, 7.08; N, 7.14. C21 H26 N2 O3. HCl requires C, 64.52; H, 6.96; N, 7.17%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethoxy)-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; John Wyeth & Brother Limited; US3992389; (1976); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 a solution of methyl 3-hydroxy-5-methoxybenzoate (Chakraporty, T. K. and Reddy, G. V. J. Org. Chem, 57, 1992, 5462.) (3.3 g, 18.1 mmol) in dry DMF (30 mL) was added K2CO3 (6.3 g, 45.3 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then ((2-bromoethoxy)methyl)benzene (3.4 mL, 21.7 mmol) was added and the mixture stirred at 160 C. for 2 hrs. The reaction was cooled down to room temperature and diluted with EtOAc, washed with water and brine, and dried over MgSO4, filtered and concentrated to give the crude product (90%) which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route ((2-Bromoethoxy)methyl)benzene, its application will become more common.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem