Category: 340825-13-0

Related Products of 340825-13-0,Some common heterocyclic compound, 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, molecular formula is C10H9IO, 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.

Intermediate 8B: (S)-N-(6-Iodo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-(methoxymethyl) pyrrolidin-1-amine To a stirred mixture of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (I-8A, 20.90 g, 77 mmol), p-toluenesulfonic acid monohydrate (0.584 g, 3.07 mmol), and cyclohexane (40 mL) was added (S)-2-(methoxymethyl)pyrrolidin-1-amine (10 g, 77 mmol) dropwise at room temperature under nitrogen. The mixture was heated with azeotropic removal of water for 5 h. The reaction mixture was diluted with ethyl acetate (20 mL) and mixed with saturated aqueous sodium bicarbonate solution (15 mL). The aqueous layer was separated and extracted with ethyl acetate (2*30 mL). The combined organic solutions were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Flash chromatography purification (330 g silica gel column, gradient elution from 0% to 20% EtOAc in hexanes) afforded (S)-N-(6-iodo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-(methoxymethyl)pyrrolidin-1-amine (29.1 g, 76 mmol) as a yellow liquid. LC/MS M+1=385.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, its application will become more common.

Reference:
Patent; Dhar, T. G. Murali; Xiao, Hai-Yun; Dyckman, Alaric J.; Chan, Eric J.; Dabros, Marta; Roberts, Daniel Richard; US2014/235591; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 340825-13-0, 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. 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, This compound has unique chemical properties. The synthetic route is as follows.

A 200 mL round bottom flask was charged with Compound 6 (4.1 g, 15 mmol),Methanol (100 mL) was added, and at 0 C. under ice cooling,Sodium borohydride (850 mg, 22.5 mmol) was gradually added,The mixture was stirred at 0 C. for 3 hours.The excess sodium borohydride was neutralized with dilute hydrochloric acid, saturated brine was added,Extraction was carried out 5 times with ethyl acetate (50 mL).The extract was washed once with ammonium chloride (100 mL)Subsequently, the solution was washed twice with saline (100 mL), dried over sodium sulfate.The filtrate was concentrated, as a pale red solid,Compound 7 was obtained (yield 3.93 g, yield 95.5%).This was used as it was for the next reaction without further purification.

The chemical industry reduces the impact on the environment during synthesis 6-Iodo-3,4-dihydronaphthalen-1(2H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RICOH COMPANY LIMITED; GOTO, DAISUKE; YAMAMOTO, SATOSHI; MIYAGAWA, SATOSHI; KATO, TAKUJI; MOHRI, MASATAKA; NAKANOTANI, HAJIME; (65 pag.)JP6146001; (2017); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 340825-13-0, 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. 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Alternative Procedure: A solution of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) until the reaction was completed as judged by LCMS (175 mL of the mCPBA solution was needed). The mixture was cooled in an ice bath, filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white amorphous solid.

The synthetic route of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Marcoux, David; Beaudoin Bertrand, Myra; Dhar, T.G. Murali; Yang, Michael G.; Xiao, Zili; Xiao, Hai-Yun; Zhu, Yeheng; Weigelt, Carolyn A.; Batt, Douglas G; (154 pag.)US2018/127368; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, 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. Recommanded Product: 340825-13-0

A solution of JR-2-methyl-CBS-oxazaborolidine (MCBSOB, 3.7 mL (3.7 mmoles) 1.0 M in toluene) and borane-diethylaniline complex (BDEA, 7.5 mL, 42 mmoles) in 40 mL toluene was heated to 30. A solution of 6-iodo-3,4-dihydro-2H-naphthalen-l-one (10 grams,36.8 mmoles) in 40 mL toluene was added dropwise over 2.5 hours. The reaction mixture was stirred for an additional 0.5 hour at 30. To the solution (at room temperature) was added 20 mL methanol. After 0.25 hour, 50 mL IN hydrochloric acid was added slowly. The mixture was stirred for 20 minutes then it was extracted with 200 mL ethyl ether. The organic phase was washed with IN hydrochloric acid, water, and saturated sodium chloride . The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. To the oily residue was added 100 mL hot hexane. When crystallization was complete, the white solid was collection and dried to give S-6- iodo-l,2,3,4-tetrahydro-naphthalen-l-ol, 9.62 grams (95%). m.p. 102-103, M+’ = 274, [alpha]D = +12.2 (c = 1, chloroform).

The synthetic route of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2006/66790; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 340825-13-0, 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 340825-13-0 as follows.

Alternative Procedure: A solution of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) until the reaction was completed as judged by LCMS (175 mL of the mCPBA solution was needed). The mixture was cooled in an ice bath, filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white amorphous solid.

According to the analysis of related databases, 340825-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Marcoux, David; Beaudoin Bertrand, Myra; Dhar, T.G. Murali; Yang, Michael G.; Xiao, Zili; Xiao, Hai-Yun; Zhu, Yeheng; Weigelt, Carolyn A.; Batt, Douglas G; (154 pag.)US2018/127368; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, belongs to iodides-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 340825-13-0, Application In Synthesis of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one

A solution of 6-iodo-3,4-dihydronaphthalen-1(2B)-one (5.0 g, 18.38 minol), 4- fluorobenzenethiol (4.11 mL, 38.6 minol) and absolute ethanol (20 mL) was cooled with an ice-water bath and bubbled with HC1 gas until saturation was reached (observed by theformation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in ether (250 mL) and washed sequentially with water (2 x 125 mL), 0.5 M aqueous Na2CO3 (3 xlOO mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.2 g) which was a mixture of thioketal and vinyl sulfide. The solid was dissolved in chloroform (150 mL) andcooled in an ice-water bath. A solution of mCPBA (35 g, 156 minol) in DCM (200 mL)was washed with brine (50 mL), dried, filtered, and the filter cake was washed with DCM(50 mL). The combined filtrates were added dropwise in portions to the chloroformsolution of the products from above until the reaction was completed as judged by LCMS(175 ml. of the mCPBA solution was needed). The mixture was cooled in an ice bath,filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueousNa2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2 x 120 mL), 10% aqueous Na2CO3 (3 x 200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4- fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white foamy solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BATT, Douglas G.; DHAR, T.G. Murali; (146 pag.)WO2018/71314; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 340825-13-0

According to the following reaction formula (scheme),Compound (3) was synthesized. A 200 mL round-bottom flask was charged with Compound (2) (4.1 g, 15 mmol) and methanol (100 mL). Sodiumborohydride (850 mg, 22.5 mmol) was gradually added to the resultant mixture at 0C with ice cooling, followed by stirring for 3 hours at 0C. Subsequently, excessive sodium borohydride was neutralized with dilute hydrochloric acid, and saturated brine was added to the mixture, which was then extracted with ethyl acetate (50 mL) 5 times. The extraction liquid was washed with ammonium chloride (100 mL) once and with brine (100 mL) twice. The reafter, sodium sulfate was added thereto, followed by filtration. The filtrate was concentrated to obtain Compound (3) as a pale red solid (yield amount: 3.93 g, yield rate ^ 95.5%), which was directly used in the next step without any further purification. The analysis results of Compound (3) are shown below.iH NMR (500 MHz, CDC13, TMS, delta) : 1.71 (d, 1H, J = 5.8 Hz), 1.84-2.02 (m, 4H), 2.65-2.71 (m, 1H), 2.75-2.81 (m, 1H), 4.72 (d, 1H, J =4.6 Hz), 7.17 (d, 1H, J = 8.0 Hz), 7.47 (s, 1H), 7.52 (d,t 1H, Ji = 8.0 Hz, J2 = 1.2 Hz) Mass spectrometry: GC-MS m/z = 274 (M+) Melting point: 82.0C-84.0C From the above analysis results, it was confirmed that a structure of the synthesized product did not contradict that of Compound (3).

The synthetic route of 340825-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICOH COMPANY, LTD.; GOTO, Daisuke; YAMAMOTO, Satoshi; SAGISAKA, Toshiya; KATO, Takuji; TANO, Takanori; SHINODA, Masato; MATSUMOTO, Shinji; MOHRI, Masataka; YUTANI, Keiichiro; WO2011/158953; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 340825-13-0,Some common heterocyclic compound, 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, molecular formula is C10H9IO, 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.

Intermediate 8B: (S)-N-(6-Iodo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-(methoxymethyl) pyrrolidin-1-amine To a stirred mixture of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (I-8A, 20.90 g, 77 mmol), p-toluenesulfonic acid monohydrate (0.584 g, 3.07 mmol), and cyclohexane (40 mL) was added (S)-2-(methoxymethyl)pyrrolidin-1-amine (10 g, 77 mmol) dropwise at room temperature under nitrogen. The mixture was heated with azeotropic removal of water for 5 h. The reaction mixture was diluted with ethyl acetate (20 mL) and mixed with saturated aqueous sodium bicarbonate solution (15 mL). The aqueous layer was separated and extracted with ethyl acetate (2*30 mL). The combined organic solutions were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Flash chromatography purification (330 g silica gel column, gradient elution from 0% to 20% EtOAc in hexanes) afforded (S)-N-(6-iodo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-(methoxymethyl)pyrrolidin-1-amine (29.1 g, 76 mmol) as a yellow liquid. LC/MS M+1=385.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, its application will become more common.

Reference:
Patent; Dhar, T. G. Murali; Xiao, Hai-Yun; Dyckman, Alaric J.; Chan, Eric J.; Dabros, Marta; Roberts, Daniel Richard; US2014/235591; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 340825-13-0, A common heterocyclic compound, 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, molecular formula is C10H9IO, 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.

In a tubular reactor, 6-iodolinone (81.6 mg, 0.3 mmol, 1.0 equiv.) And dimethyl sulfoxide (117.0 mg, 1.5 mmol, 5.0 equiv.) Were added in this order.And iodine (114.3 mg, 0.45 mmol, 1.5 equiv.),After being vacuumed and protected by nitrogen, it was placed at 80 C and stirred for 12 hours. After the reaction was completed,After cooling to room temperature, 5 mL of saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and extracted 3 times with ethyl acetate (5 * 3 mL). Combine the organic phase,Dry with anhydrous sodium sulfate and spin-dry to obtain the pure product. The product separation yield was 85%.

The synthetic route of 340825-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xinyang Normal University; Ma Xiantao; Yu Jing; Fan Yu; Zhang Qian; Tang Lin; (10 pag.)CN111116436; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com