Tag: M.W=200-300

Synthetic Route of 314084-61-2,Some common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, molecular formula is C11H15Br, 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.

Under a nitrogen atmosphere, 14.2 g of malonic acid dinitrile are added at normal pressure and room temperature to a mixture of 48 g of a 50% aqueous solution of sodium hydroxide and 300 g of 1-methyl-2-pyrrolidone. The reaction mixture is heated to from 60 to 100C, and 98 g of diluent are distilled off under reduced pressure (from 25 to 30 mbar). Under a nitrogen atmosphere, 45.5 g of 2-bromo-1, 3-diethyl-5-methylbenzene are added at normal pressure. The reaction mixture is then heated to 130C with stirring. At that temperature, a mixture of 0.26 g of TRIPHENYLPHOSPHINE, 0.2 g of a commercially available palladium (lI) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.071 g of Pd (LI) chloride and 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-methyl-2-pyrrolidone is added. The mixture is stirred at from 125 to 130C for a further 3 hours and then 199 g of diluent are distilled off at reduced pressure (from 20 to 25 mbar) at from 90 to 100C. After cooling to room temperature, the reaction mixture is added to 126 g of water. 4.5 g of Hyflo (Celite) are added thereto, and the mixture is stirred for 30 minutes at 40C before being filtered. The filter cake is washed with 114 g of water. Following the addition of 45 g of 32% hydrochloric acid to the filtrate (a pH value of less than 5 is then established), the precipitated solid is filtered off and washed with 120 g of water. After drying, 42.8 G (content 97.3%, yield 98.0%) of 2- (2, 6-diethyl-4- METHYLPHENYL) MALONIC acid dinitrile having a melting point of from 79 to 82C are obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3-diethyl-5-methylbenzene, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4263-52-9, 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. 4263-52-9, name is Sodium 2-bromoethanesulphonate belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 1-(2,2-diferrocenylpropane) methyl-imidazole (1.68g, 3.42mmol) and sodium 2-bromoethanesulphonate (0.72g, 3.42mmol) were refluxed at 80C for 16h in DMF (50mL). After cooling to room temperature, the reaction mixture was washed with H2O, and partitioned between H2O and CH2Cl2. The combined organic extract was dried (MgSO4) and concentrated. The residue was purified by silica gel (100-200mesh) chromatography to yield 2 (0.68g, 28%) as an orange-yellow solid. M.p. 46-47C. 1H NMR (400MHz, CDCl3): delta 9.22 (d, 1H, J=28.4Hz, NCHN), 7.50 (d, 1H, J=14.4Hz, NCH), 7.07 (d, 1H, J=7.6Hz, NCH), 5.10 (d, 2H, J=60.4Hz, CH2), 4.59 (s, 2H, CH2), 4.35-3.97 (m, 17H, Cp-H), 3.33 (s, 2H, CH2), 1.66-1.42 (m, 6H, CH3). 13C NMR (101MHz, CDCl3): delta 136.53 (N=C), 122.84 (N=C), 120.82 (N=C), 103.35 (N-CH2-Cp), 102.71 (N-CH2), 78.65 (Cp), 78.38 (Cp), 69.75 (Cp), 69.02 (Cp), 68.18 (Cp), 66,94 (Cp), 50.68 (Cp), 49.78 (Cp), 46.62 (CH2), 33.11 (CH3), 30.50 (CH3). MS (ESI) m/z 701.75 [M]+, 622.83 [M-Br]+, 599.08 [M-Br-Na]+, 78.83 [Br]- Cal. 702. IR (KBr cm-1): upsilon 3094 (=C-H), 2973 (C-H), 1640 (C=C), 1562 (C=N), 1447 (S=O), 1357, 1201, 1106, 1042, 1001, 817, 739, 479. HRMS (M-Br-Na)+: calcd 600.0828, obsd 600.0822.

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, Sodium 2-bromoethanesulphonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Su, Zhi-Ming; Ye, Hong-Min; Zhu, Xiao-Xiao; Xie, Li-Li; Bai, Sha; Yuan, Yao-Feng; Journal of Organometallic Chemistry; vol. 750; (2014); p. 162 – 168;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, 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. Computed Properties of C9H12BrN

A mixture of (3-bromo-benzyl)-dimethyl-amine (1.10 g; 5.14 mmol), ethyl acrylate (0.8 ml; 7.70 mmol), tri-o-tolyl-phosphane (156 mg; 0.53 mmol), Pd(OAc)2 (40 mg; 0.16 mmol) and NEt3 (1.4 ml; 10.0 mmol) is heated under reflux for 8 h. The reaction mixture is evaporated and the residue is subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) to give the compound (800 mg; 3.43 mmol).

The synthetic route of 1-(3-Bromophenyl)-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; EP1598353; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 393-36-2, These common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, 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.

4-Bromo-3-(trifluoromethyl)aniline was converted into 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1. According to Method C1a, 4-bromo-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)-2-chloroaniline to afford the urea. Entry 87: According to Method A2, Step 4, 4-amino-2-chlorophenol was reacted with 4-chloro-N-methyl-2-pyridinecarboxamide, which had been synthesised according to Method A2, Step 3b, to give 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)-3-chloroaniline.

The synthetic route of 393-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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.

Preparation 67 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane To a solution of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (1.5 g, 6.3 mmol) in N,N-dimethylformamide (12.7 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.6 g, 6.3 mmol), potassium acetate (1.9 g, 19.0 mmol), and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.3 g, 0.32 mmol). The reaction mixture was heated at 80 C. for 18 h, then the reaction mixture was diluted with Et2O and washed with water. The organic layers were separated, dried with Na2SO4, filtered, concentrated in vacuo, and purified by silica gel chromatography eluting with 0-100% acetone in hexanes to yield a brown oil (0.9 g, 50%): 1H NMR (400 MHz, DMSO-d6) delta 7.55 (d, J=8.0 Hz, 1H), 7.53 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 1.30 (s, 12H); 19F NMR (376 MHz, DMSO-d6) delta -49.26 (s); EIMS m/z 284.

The synthetic route of 33070-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Eckelbarger, Joseph D.; Epp, Jeffrey B.; Fischer, Lindsey G.; Lowe, Christian T.; Petkus, Jeff; Roth, Joshua; Satchivi, Norbert M.; Schmitzer, Paul R.; Siddall, Thomas L.; US2014/274701; (2014); 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. 22364-29-0, name is 2-Bromo-4,5-dimethylaniline, A new synthetic method of this compound is introduced below., COA of Formula: C8H10BrN

To a suspension of aniline ii (20.0 g, 100 mmol) in H2O (50 mL)was added 12 M HCl (100 mL) and the reaction mixture was cooled to 0 C, to which was gradually added NaNO2 (8.99 g, 130 mmol) in H2O (30 mL) followed by CuCl (12.1 g, 122 mmol) dissolved in 12 M HCl (30 mL) at same temperature. After warmed up to room temperature, the reaction was stirred for further 20 min. The products were extracted with Et2O (X3), and the combined organic extracts were washed with 25% NH3 aq. and brine, dried (Na2SO4), and concentrated in vacuo. Purification of the crude products by recrystallization from MeOH gave 1-bromo-2-chloro-4,5-dimethylbenzene (iii) (15.2 g, 69.2%) as colorless prisms.

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; Eda, Shohei; Hamura, Toshiyuki; Molecules; vol. 20; 10; (2015); p. 19449 – 19462;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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 1 : tert-Butyl 3-bromo-5-(tert-butvnbenzoate (P11a)n-BuLi (7.2 mL, 18.0 mmol, 2.5M in THF) was added to a flask under N2 containing toluene (9 mL) at -10C. >BuMgCI (4.5 mL, 9.0 mmol, 2M in THF) was then added at such a rate to keep the temperature below -5C. The resulting milky slurry was aged at -10C for 30 min, then 1 ,3- dibromo-5-(terf-butyl)benzene (6.2 g, 21.2 mmol) dissolved in toluene (20 mL) was added. The rate of addition was such that the temperature did not increase above -5C. After addition was complete, the mixture was kept at -10C until the metal-halogen reaction was complete. A solution of di-tert-butyl dicarbonate (5.89 g, 27 mmol) in toluene (7.5 mL) was then charged such at a rate to keep the temperature below -5C. After the addition was complete, the mixture was kept at -10C until the aryl-Mg intermediate was completely consumed. The mixture was quenched by the addition of 10% aq. citric acid (40 mL). The phases were separated and the organic layer was washed with another 10% aq. citric acid (40 mL). The organic extracts were dried over MgS04 and concentrated. Compound P11a (4.0 g, 60%) was obtained as a brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 4263-52-9, name is Sodium 2-bromoethanesulphonate, 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. Quality Control of Sodium 2-bromoethanesulphonate

b) Compound lb; [0169] A mixture of compound la, (0.1 g, 0.45 mmole), sodium 2- bromoethanesulfonate (0.19 g, 2 equivalents) and 2,6-di-tert-butylpyridine (99 muL, 0.45 mmole) in [BMIM]BF4] (1 mL, Aldrich) was heated in an oil bath at 150C with vigorous stirring for 16 hours. The reaction was then cooled to room temperature and a small portion of the reaction mixture was withdrawn, diluted with methanol/water and analyzed by analytical HPLC using a Phenomenex, Ci8,4.6 x 250 mm column and a 30 minute gradient of 10? 70% MeCN/water (with 0.05% TFA) at a flow rate of 1.0 mL/minute and UV detection at 260nm and 220 nm. Product was observed eluting at Rt = 13.3 minutes (-40% conversion). The reaction mixture was prepared by diluting it with water (15 mL) and washing this solution with ethyl acetate (2 x 25 mL). The aqueous solution was then treated with 3 to 4 drops of ammonia and further extracted with ethyl acetate (2 x 25 mL). The aqueous solution was then concentrated to about 7 mL by rotary evaporation. The product was then purified by preparative HPLC using an YMC, Ci8, 30 x 250 mm column and the same gradient as described above at a flow rate of 20 mL/minute. HPLC fractions containing product were combined and concentrated under reduced pressure. Yield = 30 mg (20%, white solid); MALDI-TOF MS 330.6 observed.

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

Reference:
Patent; SIEMENS HEALTHCARE DIAGNOSTICS INC.; NATRAJAN, Anand; SHARPE, David; WEN, David; JIANG, Qingping; WO2011/146595; (2011); A2;,
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. 64695-79-0, name is 2-Bromo-4,5-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4,5-difluoroaniline

To a mixture of compound 47a (10 g, 48.08 mmol) and compound 47b (20.84 g, 57.69 mmol) in toluene (200 mL) was added Pd (PPh3) 4 (2.78 g, 2.4 mmol) in one portion under N 2. The resulting black mixture was stirred at 100C for 12 h under N 2. The reaction was cooled to 25C and then treated with 6N HCl (10 mL) with stirring at 25C for 1h. It was diluted with water (400 mL) and extracted with EtOAc (120 mL 3). The combined organic layers was washed with 20%KF solution (200 mL) and brine (100 mL) successively, dried over sodium sulfate and concentrated in vacuum to give the crude product, which was purified by column chromatography on silica gel (5%EtOAc in petroleum ether) to give compound 47c (4.2 g, 51% yield) as a yellow solid. LCMS: R t = 0.709 min in 5-95AB_220&254. lcm chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z=171.9 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.50 (dd, J=8.8 Hz, 11.2 Hz, 1H), 6.41 (dd, J=6.8 Hz, 12.0 Hz, 1H), 6.37-6.17 (m, 2H), 2.52 (s, 3H).

The synthetic route of 64695-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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 16518-62-0, SDS of cas: 16518-62-0

In a two-necked 200 mL round-bottom flask, Mg turnings (5.30 g, 216 mmol, 10.0 equiv) were flame-dried under vacuum. Upon cooling to room temperature, THF (55 mL), 3-bromo-N,N-dimethylaniline (6.50 g, 32.4 mmol, 1.50 equiv) as a solution in THF (55 mL) and a crystal of I2 were added. The flask was fitted with a reflux condenser and the solution vigorously stirred. Once the resulting exotherm had subsided, the reaction mixture was heated to reflux (70 ¡ãC) for 1h. This Grignard reagent was then allowed to cool to room temperature and added to a cooled solution of 2-bromobenzaldehyde (4.00 g, 21.6 mmol, 1.00 equiv) in THF (32 mL) at 0 ¡ãC via cannula over 10 mm. The reaction mixture was then allowed to reach room temperature and stirred for 12 h and quenched with sat. aq. NH4Cl (75 mL). The aqueous phase was then extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica (1percent to 5percent EtOAc in hexanes) provided the desired (2-bromophenyl)(3-(dimethylamino)phenyl)methanol (S8) (6.36 g, 20.8 mmol, 96percent yield) a yellow viscous oil: Rf 0.4 (20percent EtOAc in hexanes); 1H NMR (500 MHz, CDC13) oe 7.59 (dd, J= 7.7, 1.6 Hz, 1 H), 7.53 (dd, J= 7.9, 1.1 Hz, 1 H), 7.33 (td, J= 7.5, 1.0 Hz, 1 H), 7.20 (t, J= 7.9, 1 H), 7.13 (td, J= 7.7, 1.6 Hz, 1 H), 6.84 (bs, 1 H),6.72 (d, J= 7.5, 1 H), 6.66 (dd, J= 8.2, 2.2 Hz, 1 H), 6.16 (s, 1 H), 2.93 (s, 6 H), 2.38 (bs, 1 H); 13C NMR (125 MHz, CDCl3) oe 150.8, 143.3, 142.9, 132.9, 129.3, 129.1, 128.7, 127.8, 123.1,115.3, 112.2, 111.4, 75.3, 40.8; IR (neat) 3392 (bs), 2917 (s), 2848 (s), 1604 (s), 1498 (s), 1437 (s), 1353 (s), 1018 (m), 996 (s), 744 (s) cm?; HRMS (ES) m/z calculated for C15H17NOBr [M+H] 306.0494, found 306.0492.

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; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; HOYE, Adam, T.; KIM, Won-suk; MARTINEZ-SOLORIO, Dionicio; SMITH, Amos, B.; SANCHEZ, Luis; TONG, Rongbiao; NGUYEN, Minh, Huu; WO2013/185021; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary