Month: June 2021

Synthetic Route of 454-79-5, 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. 454-79-5 name is 2-Bromo-5-(trifluoromethyl)aniline, 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.

A resealable tube was charged with 2-bromo-5- (trifluoromethyl)aniline (1.00 g, 4.16 mmol), 1- dimethylamino-2-propyne (0.520 g, 6.20 mmol), PdCl2(PPh3J2 (0.15 g, 0.21 mmol), copper iodide (0.80 mg, 0.42 mmol), diisopropylethylamine (1.0 mL) and acetonitrile (3.0 mL) . The system was purged with argon, the tube sealed and the mixture stirred at room temperature for 20 h. The reaction EPO mixture was filtered through celite and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-dichloromethane) to afford 2- (3-dimethylamino-l-propynyl) -5- (trifluoromethyl)aniline as a brown oil. MS m/z = 243 [M+H]+. CaIc’d for C12H13F3N2: 242.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, belongs to bromides-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. name: 1-(2-Bromophenyl)-N-methylmethanamine

A mixture of compound 1A (4.30 g), [N-Boc-glycine] (3.01 g, 17.1 mmol), EDC (3.28 g, 17.1 mmol), and HOAt (2.34 g, 17.1 mmol) in DCM (50 ml) was stirred at rt overnight. The reaction was quenched with the addition of sat’d NaHCO3 solution. The organic layer was separated, washed with brine, dried MgSO4), and concentrated to give the crude product which was purified by flash chromatography (10-20% EtOAc/ hexane) to give compound 1B (3.35 g) as a colorless film.

The synthetic route of 698-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2004/788; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 698-00-0,Some common heterocyclic compound, 698-00-0, name is 2-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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: Under air, 1 (0.2 mmol), NH4I (0.8 mmol), 70% TBHP in water (2.4 mmol) and DMSO (0.5 mL) were added to a 10 mL Schlenk tube sealed with a Teflon lined cap. The reaction mixture was stirred at 90 C for 4 h in an oil bath. Upon completion, the reaction mixture was left to cool to room temperature and slowly quenched with anhydrous sodium sulfite. The reaction mixture was then diluted with ethyl acetate (5 mL) and then washed with water (5 × 5 mL). The aqueous layer was extracted with EtOAc (3 × 5 mL). The combined organic layers were dried over Na2SO4. The filtrate was concentrated and the crude product was purified by column chromatography on silica gel with petroleum ether (60-90 C)/ethyl acetate eluent. Characterisation data are consistent with literature data.

The synthetic route of 698-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shao, Ying; Zheng, Hao; Wu, Zhuhong; Huang, Lei; Tong, Jingjing; Wu, Ming; Sun, Xiaoqiang; Journal of Chemical Research; vol. 41; 9; (2017); p. 504 – 508;,
Bromide – Wikipedia,
bromide – Wiktionary

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 18599-22-9 as follows. Safety of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

To a stirred solution of silver acetate (10 mg, 0.060 mmol) in glacial acetic acid (20 mL) at reflux temperature was added zinc powder (10 g, 153 mmol) in one portion, and the whole was stirred at that temperature for additional 30 seconds. After refluxing for 30 seconds, the flask was cooled by dipping in an ice-bath. The Zn-Ag couple formed was separated by vacuum filtration in the open-air, which was washed with Et2O several times, followed by drying under reduced pressure. The Zn-Ag couple separated was stored at room temperature under Ar atmosphere. See Figure S1 Preparation of CH2=CHCF2CF2ZnBr in DMF (2-Zn) In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, was placed Zn-Ag couple (0.66 g, 10 mmol) in DMF (5.0 mL). To the suspension was slowly dropwise added 4-bromo-3,3,4,4-tetrafluorobut-1-ene (1, 1.0 g, 5.0 mmol) at 0 C and the whole was stirred at that temperature for 30 min. The resultant was subjected to a short pad of celite and washed by Et2O three times. The filtrate was concentrated in vacuo to give the corresponding organozinc reagents 2-Zn in 86% NMR yield as a 0.70 M DMF solution (1,1,2,2-Tetrafluorobut-3-en-1-yl)zinc bromide in DMF (2-Zn) Yield: 86% (determined by 19F NMR); 19F NMR (CDCl3): 112.10 (brs, 2F, CF2CH), 120.23 (brs, 2F, CF2Zn).

According to the analysis of related databases, 18599-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5BrFN

General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 mol% of 5 in 2 mL N,N-dimethylformamide). The reaction mixture was stirred at 130 C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 mol% of catalyst 5 was applied.

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 1003-98-1.

Reference:
Article; Srinivas, Keesara; Saiprathima, Parvathaneni; Balaswamy, Kodicherla; Ra, Mandapati Mohan; Journal of Organometallic Chemistry; vol. 741-742; 1; (2013); p. 162 – 167;,
Bromide – Wikipedia,
bromide – Wiktionary

5910-12-3, name is 3-Bromopyrazolo[1,5-a]pyridine, belongs to bromides-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. Computed Properties of C7H5BrN2

REFERENCE EXAMPLE 1 3-(6-Fluoropyridin-2-yl)pyrazolo[1 ,5-a]pyridine To a 3-bromopyrazolo[1 ,5-a]pyhdine (2.40 g, 12.17 mmol) solution in DME (54 mL) under argon atmosphere, 6-fluoro-2-pyhdylboronic acid (1.80 g, 12.77 mmol), Pd(PPh3)4 (1.40 g, 1.21 mmol) and a solution of K2CO3 (3.70 g, 26.8 mmol) in H2O (7 mL) were added. The resulting mixture was heated at 85 0C for 5 h, cooled and concentrated to dryness. The crude product obtained was chromatographed over silica gel using hexane/EtOAc mixtures of increasing polarity as eluent, to afford 1.21 g of the desired compound (47% yield). LC-MS (Method 2): tR = 3.00 min; m/z = 214 (MH+).

The synthetic route of 5910-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PALAU PHARMA, S. A.; SALAS SOLANA, Jorge; ALMANSA ROSALES, Carmen; COMELLES ESPUGA, Josep; FONTES USTRELL, Montserrat; SOLIVA SOLIVA, Robert; PASTOR PORRAS, Jose, Javier; WO2010/72823; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 185122-74-1, 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. 185122-74-1, name is 5-Bromo-2,3-dihydro-1H-inden-1-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-bromo-2,3-dihydro-lH-inden-l -amine (2.2 g, 10.4 mmol) andSodium bicarbonate (2.6 g, 31.2 mmol)Suspended in acetonitrile (100 mL)The mixture was cooled to 0 C,To this was added Boc anhydride (3.4 mL, 15.6 mmol).The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure.The residue was taken up in ethyl acetate (100 mL) and the resulting solution was washed with water (50 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 20/1)The title compound was obtained as a white solid (3.3 g, 100%).

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, 5-Bromo-2,3-dihydro-1H-inden-1-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 698-00-0, A common heterocyclic compound, 698-00-0, name is 2-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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.

General procedure: TMSCN (0.15 mL, 1.0 mmol) was added to a stirred mixture of PIFA (430 mg,1.0 mmol) and 3.0 mL of DCE at room temperature. After 40 min, Na2SO4(36 mg, 0.25 mmol) and tertiary amine (0.5 mmol) were then added to themixture successively and reacted for overnight. Subsequently,the mixture was poured into aqueous NaHCO3 solution and Na2S2O3solution and extracted with dichloromethane. The organic layer was washedwith brine, dried over sodium sulfate and concentrated in vacuo. Purificationby column chromatography on silica gel produced alpha-aminonitriles.

The synthetic route of 698-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Hang; Zhang, Xiaohui; Liu, Qing; Pan, Jing; Hu, Wen; Xiong, Yan; Zhu, Xiangming; Tetrahedron Letters; vol. 56; 41; (2015); p. 5628 – 5631;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 51554-93-9,Some common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, molecular formula is C14H21Br, 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 1 -bromo-4-octylbenzene (3.733 g; 12.48 mmol;) in dry THF (20.0 cm3) at -78 C was added n-BuLi (5.0 cm3; 12.5 mmol). The mixture was stirred at -78 C for 2 hours to yield a pale-yellow clear solution. The solid of diethyl 2,5-di(thieno[3,2-b]thiophen-2-yl)terephthatate (3) (1.30 g; 2.60 mmol) was added in one portion and the mixture (a yellow suspension) was stirred at -78 C for 20 minutes. The cooling bath was removed and the mixture was stirred at 22 C for 50 hours to yield a deep yellow clear solution. Saturated ammonium chloride solution (50 cm3) was added and the mixture was stirred for 15 minutes. The orange oil was taken into diethyl ether (2 x 50 cm3). The solvent was concentrated till a yellow solid started crashing out. Methanol (50 cm3) was added to the residue and the precipitate was collected by suction filtration and washed with methanol.The solid was dissolved in dry DCM (50 cm3) andBF3 etherate (1.0 cm3; 8.10 mmol) was added. The blue clear solution was stirred at 22 C for 1 hour followed by the addition of methanol (150 cm3). The yellow precipitate was suction filtered off and washed with methanol. The solid was further purified by flash column chromatography on silica (9:1 petroleum ether 40- 60-chloroform) to yield the productas a bright-yellow solid (1.06 g, 36%). *H-NMR (CDCI3, 300 MHz): delta= 0.86 (t, J = 6.7 Hz, 6H), 1.25 (m, 20H), 1.58 (m, 4H), 2.54 (t, J = 7.8 Hz, 4H), 7.07 (d, J = 8.3 Hz, 4H), 7.18 (d, J = 8.3 Hz, 4H), 7.25 (d, J = 5.2 Hz, 1H), 7.27 (d, J = 7.2 Hz, 1H), 7.50 (s, 1H).

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-4-octylbenzene, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; WANG, Changsheng; TIERNEY, Steven; D’LAVARI, Mansoor; NANSON, Lana; WO2013/10614; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 58534-95-5, 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. 58534-95-5 name is 3-Bromo-2-fluoroaniline, 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.

General procedure: A 100 mL round bottom flask equipped with a stirbar and condenser was charged with 3-bromo-2-methylaniline (2.74 ml, 22.25 mmol), sodium 3-nitrobenzenesulfonate (8.93 g, 39.7 mmol), and 2-methylpropane-1,2,3-triol (6.61 g, 62.3 mmol). The mixture was then taken up in water (3.85 mL) and then carefully treated with concentrated sulfuric acid (7.12 mL). The reaction mixture was then heated to 150 C with stirring. After reaching 140 C the reaction was stopped and all glassware was washed alternatingly with 1 N aq sodium hydroxide and dichloromethane to 250 mL total volume into a 400 mL beaker equipped with a stirbar. The aqueous layer was adjusted to pH 8 with SN aq sodium hydroxide and the mixture stirred for ~1 h. The mixture wastransferred to a 1 L separatory funnel, diluted with ~400 mL dichloromethane, and the layers were separated. The resulting emulsion was treated with ~200 mL saturated brine and allowed to sit overnight to separate the layers. The organic layer was isolated and the aqueous re-extracted with an additional quantity of dichloromethane. The organics were then pooled, dried over sodium sulfate, filtered, and concentrated to a residue. Theresidue was purified by flash chromatography (15-65% dichloromethane:hexanes). Fractions containing the desired material were pooled and concentrated to a residue. The residue was then taken up in dichloromethane and extracted repeatedly with 1 N aq hydrochloric acid. The organic layer was isolated and the aqueous re-extracted with an additional portion of dichloromethane. The organics were then pooled, dried oversodium sulfate, filtered, and concentrated to afford the title compound as a light orange solid (0.995 g, 4.00 mmol, 18% yield). Following the procedure described in Example 15a using 3-bromo-2-fluoroanilineand propane-1,2,3-triol afforded the title compound as a solid (75%). 1H NMR (400 MHz,dichloromethane-d2) ppm 7.44 – 7.53 (m, 2H) 7.61 (dd, J=8.84, 6.06 Hz, 1H) 8.15 (dt,J=8.34, 1 .52 Hz, 1H) 8.92 (dd, J=4.29, 1.52 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-2-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; MOORE, Michael, Lee; PARRISH, Cynthia, Ann; SQUIRE, Michael, Damien; WO2013/52716; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary