Category: 95-15-8

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. Preparation of benzo[b]thiophene-2-carboxaldehyde. To a solution of 31.25 ml of a 1.6M solution of n-butyl lithium in hexane and 100 ml of dry diethyl ether at -20 C. was added a solution of 6.7 g of 1-benzothiophene in 100 ml of dry diethyl ether. The mixture was stirred at -20 C. for 2 hours. A solution of 3.8 ml of dimethylformamide and 10 ml of dry diethyl ether was added and the reaction was allowed to warm to 0 C. The reaction was stirred an additional 1 hour at 0 C., at which time 75 ml of 1N hydrochloric acid were added. After stirring for 15 minutes, the layers were separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and evaporated to dryness. The resulting oil was stored at about 0 C. for 3 days, at which time a solid formed. The solid weighed 8.5 g and was identified as the desired subtitled intermediate based upon the mass spectral and proton NMR data. Analysis for C9 H6 OS; Calculated: C, 66.64; H, 3,73; Found: C, 66.39; H, 3.95., 95-15-8

As the paragraph descriping shows that 95-15-8 is playing an increasingly important role.

Reference£º
Patent; Eli Lilly and Company; US4659717; (1987); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95-15-8,Thianaphthene,as a common compound, the synthetic route is as follows.,95-15-8

EXAMPLE; (Example); First step: Synthesis of 1-benzothien-2-yl(5-bromo-2-fluorophenyl)methanol; Into a tetrahydrofuran (100 liters) solution of benzo[b]thiophene (17.4 kg ) was dropwise added a n-hexane solution (56.2 kg) of n-butyl lithium (15.08%) in an argon atmosphere at -24.2 to -13.5C, followed by stirring at -22.1 to -13.5C for 40 minutes. Into this solution was dropwise added a tetrahydrofuran (18 liters) solution of 5-bromo-2-fluorobenzaldehyde (25.5 kg) at -22.1 to -11.8C, followed by stirring at -23.5 to -16.1C for 2 hours. To the reaction mixture were added water (100 liters), toluene (130 liters) and 38% hydrochloric acid (12.3 kg), and extraction was conducted. The organic layer was washed with water (130 liters) and then subjected to distillation at normal pressure to distill off the solvent until the residue became 100 liters. Toluene (130 liters) was added to the residue and the mixture was subjected to distillation at normal pressure to distil off the solvent until the residue became 100 liters. The operation of adding toluene to the residue and subjecting the mixture to distillation under reduced pressure to distill off the solvent, was repeated twice: Then, n-heptane (310 liters) was added to the residue, followed by heating to dissolve the residue. To the solution was added, as a seed crystal, about 26 g of the 1-benzothien-2-yl(5-bromo-2-fluorophenyl)methanol produced in the same manner as that shown in the first step of Reference Example 1, followed by stirring at 1.2 to 5.0C for 13 hours. The separated-out crystals were collected by filtration, washed twice with a toluene-n-heptane (1:6) mixed solvent (26 liters), and subjected to vacuum drying to obtain, as white crystals, 1-benzothien-2-yl(5-bromo-2-fluorophenyl)methanol [35.91 kg, yield: 84.8%, purity: 99% (HPLC)]. 1H-NMR (CDCl3): delta 2.74 (1H, d), 6.35 (1H, d), 6.93 (1H, dd), 7.14 (1H, s), 7.27-7.38 (2H, m), 7.39 (1H, m), 7.68 (1H, dd), 7.74 (2H, m)

The synthetic route of 95-15-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Astellas Pharma Inc.; Kotobuki Pharmaceutical Co., Ltd.; EP2105442; (2009); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95-15-8,Thianaphthene,as a common compound, the synthetic route is as follows.

1) The compound of formula 2 benzothiophene (2.68 g, 20 mmol)Dissolved in refined tetrahydrofuran, stirred under argon and 195K conditions,2.4 mol / L of n-butyllithium (9.75 mL, 23 mmol) was slowly injected,Continue low temperature reaction for half an hour. Iodomethane (3 mL, 23 mmol)Injected into the reaction flask, the reaction mixture was stirred at low temperature for an hour,Naturally rose to room temperature, adding an appropriate amount of water to terminate the reaction.Liquid separation and extraction with methylene chloride. Combine the organic phases, whirl, remove the solvent and dry. The residue was chromatographed on petroleum ether, silica gel to give 2.67 g of a colorless solid,Yield: 90%.

As the paragraph descriping shows that 95-15-8 is playing an increasingly important role.

Reference£º
Patent; Jiangxi Science and Technology Normal University; Pu Shouzhi; Liu Gang; Li Gang; (14 pag.)CN106905312; (2017); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95-15-8,Thianaphthene,as a common compound, the synthetic route is as follows.

EXAMPLE 35 1-[3-Acetylthio-3-(benzo[b]thien-2-ylcarbonyl)-2-methylpropionyl]-L-proline To a solution of 2.68 g. (0.020 mole) of benzo[b]-thiophene in 40 ml. of ether cooled at -20 C. is added 0.020 moles of n-butyl lithium (2.54 N solution in hexane). The mixture is stirred at -20 C. for 15 minutes, then is allowed to warm to room temperature. Then 2.70 g. (0.020 mole) of N-methylformamilide is added and the mixture is stirred for 24 hours. The reaction is quenched with water and the mixture is treated with saturated sodium bisulfite solution. The bisulfite addition product is collected by filtration. The wet cake is slurried in water and decomposed by the addition of solid sodium carbonate. The mixture is filtered and the solid is washed with water and dried to give 1.75 g. of benzo[b]thiophene-2-carboxaldehyde.

The synthetic route of 95-15-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US4299769; (1981); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8,95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under nitrogen protection, in a four-necked flask equipped with a mechanical stirring and a thermometer, 20.1 g of benzothiophene and 180 mL of 2-methyltetrahydrofuran were stirred and dissolved, and the temperature was lowered to -40–35 C, and 90 ml of butyllithium was added thereto. 3 hours after the reaction at the temperature, 40.3 g of 2-fluoro-5-bromobenzaldehyde was added. After the reaction was completed at this temperature for 10 hours, the temperature was raised to room temperature, and the pH was adjusted to 7 by adding hydrochloric acid. 2. Under a nitrogen atmosphere, Compound 2 and n-hexane were added to a four-necked flask equipped with a mechanical stirring and a thermometer, and the mixture was stirred and dissolved. Then, trifluoroacetic acid and triphenylsilane (5 eq) were added, and then reacted at -10 C for 1 hour. After the completion of the monitoring reaction, the temperature was raised to room temperature, and the target compound was obtained as a white solid, 41 g.The yield in two steps was 81%.

95-15-8 Thianaphthene 7221, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; Ruifuxin Jiangsu Pharmaceutical Co., Ltd.; Li Jianxin; Zhao Datong; Huang Jian; Xu Xiangyu; Zhang Zhiguo; Wang Jianfa; (11 pag.)CN108623558; (2018); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95-15-8,Thianaphthene,as a common compound, the synthetic route is as follows.

a 2-Bromobenzothiophene 94.0 g (0.7 mol) of benzothiophene in 940 ml of absolute diethyl ether are initially taken at 20-30 C., and 332 g (0.77 mol) of a 15% strength solution of n-butyllithium in n-hexane are added dropwise in the course of 2 hours. After one hour, 127 g (0.799 mol) of bromine are added dropwise, also at 0 C., and stirring is continued for 2 hours. After working up was carried out in a conventional manner, 2-bromobenzothiophene is distilled off, finally at 1-1.2 mmHg and 84-86 C. Yield: 240 g (76%).

95-15-8 Thianaphthene 7221, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; BASF Aktiengesellschaft; US5110829; (1992); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95-15-8

Under inert conditions benzo[b]thiophene (7.00 g, 51.1 mmol,1.00 equiv) was dissolved in dry THF and stirred for 30 min at-78 C. n-BuLi (26.6 mL, 2.5 M in hexane, 66.5 mmol, 1.30equiv) was added slowly, and the mixture was stirred for 30min. MeI (4.90 mL, 11.2 g, 78.9 mmol, 1.54 equiv) was addedover 15 min. The reaction was stirred for 20 min at -78 C, for 3h at r.t., quenched with water (100 mL), and extracted withEtOAc (4 ¡Á 50 mL). The organic layer was dried over Na2SO4, andthe solvents were removed in vacuo. After purification by flashchromatography (silica, hexane), 5 could be obtained as acolourless solid in 97% yield (7.26 g, 49.0 mmol). TLC (SiO2, hexane):Rf = 0.54. 1H NMR (400 MHz, DMSO-d6): delta = 7.85 (dp, J =7.8, 0.7 Hz, 1 H), 7.74-7.64 (m, 1 H), 7.35-7.21 (m, 2 H), 7.12 (p,J = 1.2 Hz, 1 H), 2.56 (d, J = 1.2 Hz, 3 H) ppm. 13C NMR (101 MHz,DMSO-d6): delta = 140.57, 140.09, 138.88, 124.19, 123.46, 122.57,122.05, 121.78, 15.74 ppm. MS (EI): m/z [M]+ calcd for C9H8S:148.0342; found: 148.0341.

95-15-8 Thianaphthene 7221, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Hofsaebeta, Robert; Rombach, David; Wagenknecht, Hans-Achim; Synlett; vol. 28; 12; (2017); p. 1422 – 1426;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

95-15-8, EXAMPLE 11 Preparation of Benzo[b]thiophene-2-carboxaldehyde STR100 Butyllithium (54 mL, 134 mmol) is added dropwise to a solution of N,N,N’,N’-tetramethylethylenediamine (15.57 g, 134 mmol) in tetrahydrofuran under nitrogen at 0 C. The reaction mixture is treated dropwise with a solution of benzothiophene (15.00 g, 112 mmol) in tetrahydrofuran, warmed to room temperature, treated with additional N,N,N’,N’-tetramethylethylenediamine (15.57 g, 134 mmol) and butyllithium (54 mL, 134 mmol), stirred at room temperature for 13 hours, cooled to 0 C., treated with N,N-dimethylformamide (24.40 g, 336 mmol), warmed to room temperature, stirred for five hours, poured into one molar hydrochloric acid and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over Na2 SO4 and concentrated in vacuo to obtain an orange oil. Flash chromatography of the oil using silica gel and a 15% ethyl acetate in hexane 25 solution gives the title product as an orange oil (12.51 g, 69%).

The synthetic route of 95-15-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US5492925; (1996); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a CH2Cl2 solution (50 mL) of benzo[b]thiophene (14, 5.00 g, 37.3 mmol) and KOAc (7.30 g, 74.6 mmol) was added Br2 (3.8 mL, 74.6 mmol) at 20 C, and the solution was heated under reflux for 24 h. To the solution was added a satd solution of Na2S2O3 and NaHCO3. The organic and the aqueous layer were separated, and the latter was extracted with CH2Cl2 (3*30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash silica column chromatography (pure heptanes) to yield 15a as a white solid (9.1 g, 84%). The spectroscopic data were identical with those reported.17,18, 95-15-8

95-15-8 Thianaphthene 7221, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Tengho Toguem, Serge-Mitherand; Malik, Imran; Hussain, Munawar; Iqbal, Jamshed; Villinger, Alexander; Langer, Peter; Tetrahedron; vol. 69; 1; (2013); p. 160 – 173;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem