Tag: M.W=100-200

Electric Literature of 17247-58-4, 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. 17247-58-4 name is (Bromomethyl)cyclobutane, 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.

500 mg (2.00 mmol) of the compound from Ex. 31A and 690 mg (5.00 mmol) of potassium carbonate were stirred in 10 ml of anhydrous DMF at RT for 15 min, before 449 mul (4.00 mmol) of (bromomethyl)cyclobutane were added. Then the reaction mixture was stirred at 50 C. for about 16 h. After cooling to RT, water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The product was isolated by means of MPLC (Biotage Isolera One, SNAP KP-Sil cartridge, 50 g of silica gel, eluent: cyclohexane/ethyl acetate 2:1). After concentration of the product fractions and drying under high vacuum, 486 mg (76% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 10.07 (s, 1H), 3.96 (d, 2H), 2.82-2.69 (m, 1H), 2.76 (s, 3H), 2.66-2.58 (m, 1H), 2.04-1.91 (m, 2H), 1.89-1.74 (m, 4H), 1.07-0.96 (m, 2H), 0.73-0.64 (m, 2H). LC/MS (Method 1, ESIpos): Rt=1.89 min, m/z=319.11 [M+H]+.

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

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengesellschaft; HAERTER, Michael; KOSEMUND, Dirk; CANCHO GRANDE, Yolanda; DELBECK, Martina; KALTHOF, Bernd; LUSTIG, Klemens; SUESSMEIER, Frank; US2020/16159; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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 B: tert-Butyl [1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl]carbamate An inerted vessel was charged dichloromethane (866 kg) and cooled to -20 to -10 C. Then iso-propylmagnesium chloride solution in THF (2M, 326.1 kg, 669 mol) was slowly added followed by 1-bromo-2,5-difluorobenzene (120.1 kg, 622 mol). After 2 h at this temperature, an additional charge of iso-propylmagnesium chloride in THF solution was slowly added (2M, 58.65 kg, 121 mol) and the reaction aged 1 h. Then, a drop-wise addition of a dichloromethane solution of tert-butyl (1-[methoxy(methyl)amino]-1-oxopent-4-yn-2-yl)carbamate (70.8 kg, 276 mol in 292 kg dichloromethane) was conducted over 2 h at -20 to -20 C. The mixture was then warmed to room temperature and stirred for 10 h. The reaction was then slowly reverse quenched into aqueous ammonium chloride (175.6 kg in 1550 kg of water) at 5-10 C. The solution pH was then adjusted to ?7 by adding 68 kg of con. HCl. The layers were then separated and the aqueous extracted with dichloromethane (414 kg). The combined organics were then dried with Na2SO4, filtered, treated with activated carbon (10 kg), filtered, and concentrated to 71-141 L. A constant volume (71-141 L) vacuum distillation solvent switch to n-heptane was then performed to crystallize the product. The slurry was then cooled to 0 C. and stirred 2 h. The slurry was filtered and the cake washed with n-heptane, 2-propanol, and then water. The solids were dried under vacuum at 40-50 C. overnight to give tert-butyl [1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl]carbamate.

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-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp; Merck Sharp & Dohme Ltd.; Arroyo, Itzia Z.; Krueger, Davida; Chen, Ping; Moment, Aaron J.; Biftu, Tesfaye; Sheen, Faye; Zhang, Yanfeng; US9181262; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 10485-09-3, name is 2-Bromoindene, belongs to bromides-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 10485-09-3, Formula: C9H7Br

A 1.45 g (59.8 mmol) piece of magnesium was charged into a sufficiently dried and argon-substituted 200 mL reactor, and stirred vigorously for 30 minutes while heating under reduced pressure. After cooling to room temperature, a reflux condenser was attached, and a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred. A solution of 2.93 g (15.0 mmol) of 2-bromoindene in 15 mL of a diluted solution of tetrahydrofuran is added dropwise (1.0 mL added, followed by heating under reflux with a dryer until the color of iodine disappears, remaining drop after reaction starts) It stirred at room temperature after completion | finish for 2 hours.The reaction solution is diluted with 9.00 mL (75.3 mmol) of dimethylsilyl dichloride in 10 mL of n-hexane diluted solution.The reaction was slowly added at -78 C with cooling, and stirring was continued for 19 hours while returning to room temperature.After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 10 mL of tetrahydrofuran and 1.50 mL (16.0 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue. In a fully dried, argon purged 100 mL reactor, obtained in Synthesis Example 5-15.62 g (15.0 mmol) of the selected compound (A-5a) and 15 mL of tetrahydrofuran are added, 9.70 mL (hexane solution, 1.55 M, 15.0 mmol) of n-butyllithium solution is added, and the mixture is stirred at room temperature for 2 hours did. The above reaction was cooled to -78 C.The residue was added dropwise to the diluted solution, and stirring was continued for 45 hours while slowly returning to room temperature. Saturated aqueous ammonium chloride solution was added, the extract was extracted with ethyl acetate, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering the magnesium sulfate, the filtrate is distilled offThe residue thus obtained was purified by silica gel column chromatography to obtain 7.67 g (yield: 94%) of the target product (hereinafter referred to as compound (A-5L)) represented by the following formula (A-5L) It was obtained as a body mixture.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 452-74-4

STEP18: Synthesis of l-Bromo-4-bromomethyl-2-fluoro-benzene; To a solution of l-Bromo-2-fluoro-4-methyl-benzene (5gm, 0.026mol) in carbon tetrachloride (40ml) N-bromosuccinimide (5.6gm, 0.037mol) was added followed by addition of 400mg of Azobisobutyro nitrile(AIBN), then after reaction mixture was refluxed for 6hrs. The reaction mixture was cooled to O0C and filtered under vacuum; filtrate was evaporated under vacuum to give 6gm of l-Bromo-4-bromomethyl-2-fluoro- benzene as yellow oil. This was further used as such.

The synthetic route of 452-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TORRENT PHARMACEUTICALS LTD; WO2007/100295; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 630-17-1, 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 630-17-1 as follows.

Preparation of 4-(3,5-dimethoxy-4-(neopentyloxy)benzyl)-7-ethoxyisoquinolin-8-ol hydrochloride 39 3,5-Dimethoxy-4-(neopentyloxy)benzaldehvde EMC 380484-Hydroxy-3,5-dimethoxybenzaldehyde (500 mg, 2.74 mmol) was dissolved in DMF (7.5 ml_) and CS2CO3 (894 mg, 2.74 mmol) and neopentyl bromide (456 mg, 3.02 mmol) were added at RT and the reaction was heated at 150C for 10 min under microwave irradiation. After cooling to RT, the reaction mixture was poured into water (75 ml_) and extracted by Et2O (50 ml_). The separated organic layer was washed with water (2×50 ml_), brine (50 ml_), dried over MgSO4, filtered and dried overnight under reduced pressure to give 3,5-dimethoxy-4-(neopentyloxy)benzaldehyde EMC 38048 (274 mg, 40% yield) as yellow oil. EMC 38048MW: 252.31 ; Yield: 40%; Yellow oil.1H-NMR (CDCIs, delta): 1 .05 (s, 9H, 3xCH3), 3.72 (s, 2H, OCH2), 3.90 (s, 6H, 2xOCH3), 7.12 (s, 2H, 2xArH), 9.85 (s, 1 H, CHO).13C-NMR (CDCIs, delta): 26.4 (3xC), 32.6, 56.4 (2xC), 83.7, 107.2 (2xC), 131 .3, 144.2, 153.8, 191 .2.MS-ESI m/z (% rel. Int.): 253 ([MH+], 20), 183 (100).HPLC: Method A, XBridge column, detection UV 254 nm, RT = 6.36 min, peak area 99.9%.

According to the analysis of related databases, 630-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXONHIT S.A.; LEBLOND, Bertrand; TAVERNE, Thierry; BEAUSOLEIL, Eric; CHAUVIGNAC, Cedric; CASAGRANDE, Anne-Sophie; DESIRE, Laurent; WO2011/151423; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 399-94-0

2,5-difluorobromobenzene (15.05g, 78mmol) was dissolved in dry toluene (50mL) under nitrogen, and the ice salt bath was cooled to below -10 C. Isopropylmagnesium chloride/lithium chloride tetrahydrofuran solution was added dropwise. (66 mL, 1.3 mol/L), kept stirring at about -10 C for 1 hour.1D (10 g, 39 mmol) was dissolved in dry tetrahydrofuran (100 mL).Add dropwise to the above reaction solution, keep the temperature below -10 C, add,The reaction was carried out for 4 hours at room temperature. Lower the temperature below -10 C,Saturated ammonium chloride solution (40 mL) was added dropwise and stirred for 10 minutes.Adjust the pH to 5-6 with a 3 mol/L hydrochloric acid solution, and let stand for stratification.The aqueous phase was extracted with methyl tert-butyl ether (50 mL¡Á2) and the organic phases were combined.Wash with a saturated sodium chloride solution (30 mL ¡Á 2), and dry over anhydrous sodium sulfate.Filtration, concentration, column chromatography (petroleum ether / ethyl acetate (v / v) = 50:1-8:1),A pale yellow solid 1E (10.1 g, yield 83.5%) was obtained.

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Feng Jianchuan; Peng Fei; Chen Qingping; (45 pag.)CN105085530; (2019); B;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-99-2, name is 2-Bromo-5-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Bromo-5-fluoroaniline

Dissolve 2-bromo-5-fluoroaniline (25g, 131 mmol) in methyldisulfide (220 mL) and heat to 75 ¡ãC under nitrogen. Add isoamyl nitrite (46 mL, 342 mmol) dropwise via an addition funnel trough a reflux condenser (-1 drop/sec). Large exotherm may occur if addition is too fast. After addition is complete heat the reaction to 95 ¡ãC for 1 hour and cool to room temperature and concentrate in vacuo. Purify residue twice via silica gel chromatography eluting with hexanes to yield 22 g of 1-bromo-4-fluoro-2-methylsulfanyl- benzene (76percent). Dissolve l-bromo-4-fluoro-2-methylsulfanyl-benzene (22 g, 99.6 mmol) in dry THF (500 mL) and cool to-78 ¡ãC under nitrogen. Add butyl lithium (2. 5M in hexanes, 48 mL, 120 mmol) slowly and stir for 10 minutes after complete addition. Add trimethyl borate (22 mL, 200 mmol) and warm to room temperature. Pour into 0.1 M NaOH and extract with ether. Acidify the aqueous layer to pH 2 with concentrated HC1. Extract with ether, rry the organic layer with sodium sulfate, filter and concentrate in vacuo to yield 15.4 g (83percent) of the title compound.

The synthetic route of 1003-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 38573-88-5, 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1TERT-BUTYL 3-(2,3-DIFLUOROPHENYL)-3-HYDROXYAZETIDINE-1 – CARBOXYLATE 0 To a solution of 1 -bromo-2,3-difluorobenzene (2.48 g, 12.86 mmol) in dry diethylether (40 ml) at -780C was added dropwise n-butyllithium (2.5 M in hexane, 5.1 ml, 12.86 mmol). The mixture was stirred for 30 min after which a solution of 1 -Boc- azetidone (2.0 g, 1 1 .69 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at -780C for 30 min and then brought to ambient 5 temperature and stirred for 1 h. Aqueous saturated ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1 : 1 ) to give the title compound Yield: 1 .89 g. MS m/z (rel.0 intensity, 70 eV) 285 (M+, 1 ), 156 (68), 141 (40), 127 (63), 57 (bp).

The synthetic route of 1-Bromo-2,3-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; SONESSON, Clas; SWANSON, Lars; PETTERSSON, Fredrik; WO2010/58020; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7Br

To a solution of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (132 mg, 0.72 mmol) in THF (1.5 ml) was added dropwise n-BuLi (2.5 M in n-hexane) (0.29 ml, 0.72 mmol) at -78C under N2. The reaction mixture was stirred at -78C for 30 min. 4-(Benzyloxy)-3-bromo-5-methylbenzaldehyde (200 mg, 0.66 mmol) in THF (0.5 ml) was added dropwise at -78C. The reaction mixture was stirred at -78 C for 1 h. Saturated NH4CI (aq) was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :3 EA/PE) to yield (4-(benzyloxy)-3- bromo-5-methylphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol as a yellow oil.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 10269-01-9

General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 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:
Article; Sarkar, Rajib; Mukhopadhyay, Chhanda; Tetrahedron Letters; vol. 59; 32; (2018); p. 3069 – 3076;,
Bromide – Wikipedia,
bromide – Wiktionary