Month: November 2020

22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. 22385-77-9

To a solution of 3 (1.5 g, 5.6 mmol) in anhydrous toluene (30 mL), 1-bromo-3,5-di-tert-butylbenzene (1.8 g, 6.7 mmol), was added t-BuONa, (1.2 g 13.4 mmol), and P(t-Bu)3 (1.38 mmol, 2.8 mL of a 10 wtpercent hexane solution) under argon. After stirring under reduced pressure, Pd(dba)2 (0.16 g, 0.28 mmol) was added to the solution. The reaction mixture was stirred at 110 ¡ãC for 16 h under argon. The precipitated solid was removed by filtration, and then the residue was washed with toluene (30 mL). After addition of methanol, precipitation occurred in the solution. The solid residue after filtration was washed with methanol (30 mL), and then was recrystallized from acetone to yield 6b (2.2 g, 86percent) as a pale-yellow powder. 6b: mp: 197 ¡ãC; 1H-NMR (400 MHz, CDCl3): delta = 1.40 (s, 18H, DBC-N-Ph-C(CH3)3), 7.40 (s, 2H, aromatic ring), 7.52 (dd, 2H, J = 14.8, 7.6 Hz, aromatic ring), 7.59 (dd, 3H, J = 8.8, 3.6 Hz, aromatic ring), 7.70 (dd, 2H, J = 15.2, 7.2 Hz, aromatic ring), 7.84 (d, 2H, J = 9.2 Hz, aromatic ring), 8.03 (d, 2H, J = 7.6 Hz, aromatic ring), 9.27 (d, 2H, J = 8.8 Hz, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 31.474, 35.16, 112.04, 117.43, 122.04, 122.26, 123.35, 125.40, 126.65, 129.07, 129.11, 130.10, 136.23, 138.02, 152.77; FT-IR (nu cm-1): 3100, 3000, 2850, 1600, 1400, 1350, 1300, 1250, 900, 675; HRMS calcd. for C34H33N ([M+Na]+): 478.2505, found: 478.2506.

Statistics shows that 22385-77-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-3,5-di-tert-butylbenzene.

Reference:
Article; Hassan, Fathy; Kawamoto, Masuki; Salikolimi, Krishnachary; Hashizume, Daisuke; Hirose, Takuji; Ito, Yoshihiro; Tetrahedron Letters; vol. 59; 2; (2018); p. 99 – 102;,
Bromide – Wikipedia,
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A common heterocyclic compound, 344-03-6, name is 1,4-Dibromotetrafluorobenzene, molecular formula is C6Br2F4, 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. 344-03-6.

Synthesis of 3,3′,3″,3″‘-(3,6-dibromobenzene-1,2,4,5-tetrayl)tetrapyridine (1) To a stirred solution of 3-bromopyridine (1.0 g, 6.3 mmol) in anhydrous THF (30 mL) is dropwise added n-butyllithium (1.6M in hexane, 5.9 mL, 9.5 mmol) under nitrogen at -78¡ã C. After 1 h stirring, 1,4-dibromo-2,3,5,6-tetrafluorobenzene (0.43 g, 1.4 mmol) is added in a portion. Then, the reaction temperature is allowed to room temperature and stirs overnight. The reaction solution is quenched with water (200 mL), and the resulted mixture is extracted with chloroform. The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The mixture is purified on silica gel column chromatography using 5:1 (v/v) hexane/chloroform as eluent to give a white solid.

The synthetic route of 1,4-Dibromotetrafluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyulux, Inc.; Aguilera-Iparraguirre, Jorge; Gomez-Bombarelli, Rafael; Hirzel, Timothy D.; Cheng, Shuo-Hsien; Suzuki, Yoshitake; Yang, Yu Seok; (108 pag.)US2019/58130; (2019); A1;,
Bromide – Wikipedia,
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40161-54-4, A common compound: 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of l-bromo-2-fluoro-4-(trifluoromethyl)benzene (200 mg; 0.82 mmol)[CAS 40161-54-4] in tetrahydrofuran (15 mL) cooled to -70 C was added dropwise a solution of 1.6M n-butyllithium in n- hexane (0.7 mL; 1.1 mmol). After agitation at -70 C for 1 hour, the reaction mixture was treated dropwise with a solution of teri-butyl 4-[methoxy(methyl)carbamoyl]piperidine-l-carboxylate (247 mg; 0.91 mmol) [CAS 139290-70-3] in tetrahydrofuran (5 niL). The reaction mixture was stirred for 0.5 hours at -70 C and then for 2 hours at room temperature. The reaction mixture was deactivated with a saturated aqueous ammonium chloride solution (20 mL), then ethyl acetate (30 mL) was added. The organic layer was separated, dried over Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; petroleum ethenethyl acetate; 30:1 ; v/v) to afford teri-butyl 4-[2- fluoro-4-(trifluoromethyl)benzoyl]piperidine-l-carboxylate (180mg) as a white solid. MS m/z (+ESI): 320.1 [M-iBu+H]+.

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, 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

58971-11-2, name is 3-Bromophenethylamine, 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. 58971-11-2

A mixture of 3-bromobenzeneethanamine (9.70 g, 48,5 mmole) and 2,6-lutidine (5.8 ml, 50.0 mmole) in dry CH2Cl2 (150 ml) was cooled to 0 0C. Trifluoroacetic anhydride (5.6 ml, 40 mmole) was added dropwise; the reaction was then warmed to room temperature and allowed to stir for 24 hours. Water (120 ml) was added to the reaction, the phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 x 100 ml). The combined organic phases were washed successively with IN HCl (100 ml) and saturated NaHCO3 (100 ml), and then dried over Na2SO4, filtered, and concentrated in vacuo to provide the tile compound (12.3 g, 86%). The crude compound was used in subsequent steps. 1H NMR (400 MHz, CDCl3) delta 7.40 (d, J=8.0 Hz, IH), 7.36 (s, IH), 7.21 (t, J=7.6 Hz, IH), 7.12 (t, J=7.6 Hz, IH), 6.31 (br s, IH), 3.59 (q, J-6.8 Hz, 2H)5 2.87 (t, JK7.2 Hz, 2H).

Statistics shows that 58971-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Bromophenethylamine.

Reference:
Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2007/61458; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

111721-75-6,Some common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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.

Examples 14 and 15 2-({4-[(2,3-Dihydro[l,4]dioxino[2,3-c]pyridin-7- ylmethyl)amino]-l-piperidinyl}methyl)-9-fluoro-l,2-dihydro-4H-pyrrolo[3,2,l- iy]quinolin-4-one hydrochloride, Enantiomers 1 and 2,(a) N-(2-Bromo-3 -fluorophenyl)-3 -phenyl-2-propenamide; To a solution of 2-bromo-3-fiuoroaniline (5.29g, 27.8mmol) in acetone (12ml) was added potassium carbonate (5.75g, 41.8mmol) followed by water (15ml) and the stirred mixture cooled to 00C. Cinnamoyl chloride (4.63g, 27.8mmol) was added portionwise over 15min then the mixture stirred for a further 2h. After this time the reaction mixture was poured onto ice/water and the resulting precipitate collected and dried to yield a white solid (8.Ig). LC-MS: m/z 320/322 (MH)+.

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-3-fluoroaniline, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/3690; (2008); 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. 3814-30-0, name is (Bromomethyl)cyclopentane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3814-30-0

To a solution of 20.6 g (0.1 mol) of 4-(3,5-difluorophenyl)phenol in 200 mL of N,N-dimethylformamide in a 500 mL of three-necked flask, 4.8 g (0.12 mol) of 60% sodium hydride was added portionwise under nitrogen with stirring at 30 C., and then 16.3 g (0.1 mol) of cyclopentyl methyl bromide was added dropwise. After the reaction was stuffed for 20 hours, it was poured into 500 mL of water, and was extracted with hot petroleum ether (200 mL¡Á2). The combined organic phases was washed with water to neutral, and the solvent was then distilled off under reduced pressure. 15 g of 4-a as white crystals was obtained by recrystallization from ethanol. GC purity: 98.9%.

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO., LTD.; Yuan, Guoliang; Liang, Zhian; Wang, Kui; Hua, Ruimao; Wen, Gang; Zhang, Miaofang; Meng, Jinsong; (28 pag.)US9303208; (2016); B2;,
Bromide – Wikipedia,
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68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, 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. 68322-84-9

Example 43A 4-trans(2-bromo-4-trifluoromethyl-phenoxy)-cyclohexylamine To a stirred solution of trans-4-aminocyclohexanol (115 mg, 1 mmol) in DMF (3 mL) at 0 C. was added 60% NaH in mineral oil (120 mg, 3 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then 3-bromo-4-fluoro-1-trifluoromethyl benzene (0.17 ml, 1.2 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 338 (M+H)+.

Statistics shows that 68322-84-9 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1073-39-8, 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 1073-39-8 as follows.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (569 mg, 3.1 1 mmol, 1.00 equiv) in THF (12 mL) was added n-BuLi (2.5M in hexane, 1.30 mL, 1.05 equiv) dropwise at -78C, and the mixture was stirred at -78C for 30 min. 4-(Benzyloxy)-5-bromo-2-methoxybenzaldehyde (1 g, 3.1 1 mmol, 1.00 equiv) in THF (3 mL) was then added to the solution. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (5:1 PE/EA) to yield 1 (4-(benzyloxy)-5-bromo-2-methoxyphenyl)(1,2- dihydrocyclobutabenzen-4-yl)methanol as a light yellow oil. MS (ES) m/z: 409.0 [M-OH]+

According to the analysis of related databases, 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, the application of this compound in the production field has become more and more popular.

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

67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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. 67567-26-4

4-Bromo-2,6-difluoro-phenylamine (200 g, 0.961 mol) and N-isopropyl acetamide (107 g, 1.057 mol) in toluene (1000 mL) were stirring at 10-15 C. Phosphoryl chloride (177 g, 1.154 mol) and triethylamine (117 g, 1.156 moles) were slowly added. The reaction mixture was heated to reflux for 2-3 hours. The reaction mass was cooled to 10-15 C and water was slowly added into the reaction mixture which was stirred at 30-35 C for 15-20 minutes. The pH of the reaction mass was adjusted to 7.5-8.0 with a sodium hydroxide solution, stirred for 30 minutes at 30-35 C, and the layers were separated. The organic layer was washed with water and the layers were againseparated. Potassium hydroxide (161.5 g, 2.88 mol) and dimethylsulfoxide 400 mL at 30-35 Cwere charged to the organic layer. The reaction mixture was heated to reflux and water wasadded azeotropically for 2-4 hours at reflux temperature. The reaction mass was cooled to 25-30C and water was slowly added into the reaction mixture. The reaction mixture was stirred at 30-35 C for 15-20 minutes and the layers were separated. The organic layer was washed with anaqueous sodium chloride solution. The organic layer was concentrated under vacuum. Toluene (160 mL) and hexanes (1000 mL) were charged to the residue and the resulting mixture was stirred for 2-3 hours at room temperature. The mixture was filtered and the collected solid was washed with hexanes and dried at 50-55 C to yield 215 g (82.3%) of 6-bromo-4-fluoro-1- isopropyl-2-methyl-1H-benzoimidazole with a purity of 99.70%.

Statistics shows that 67567-26-4 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-2,6-difluoroaniline.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; INDUKURI, Anjaneyaraju; BOMMAREDDY, Aggi Ramireddy; SRINIVASARAO, Attanti Veera Venkata; JEBARAJ, Rathinapandian; CHANDUPATLA, Shivakumar; BATHARAJU, Ramesh; KUNAMNENI, Sunil; (74 pag.)WO2019/102492; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

61326-44-1, Name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, 61326-44-1, 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.

General procedure: The synthesis of intermediate tetra-brominated TPE has been reported in previous literatureS1. The solid reactant 2 (100 mg, 0.15 mmol) and solid reactant 3 (0.9 mmol), catalyst palladium acetate (1.73 mg, 0.0077 mmol) and triphenylphosphine (4.04 mg, 0.0154 mmol) was added into the cube which was pumped three times, then anhydrous and anaerobic DMF (5 ml) and bubbled triethylamine(1 ml) was injected. After quickly switching the stopper, the reaction system would flux for two days. When completed, the reaction was cooled to room temperature, then poured into a large amount of water and extracted three times with dichloromethane, and finally washed with saturated saline multiple times to obtain the organic phase. After the organic phase was dried over anhydrous sodium sulfate, the dichloromethane was swirled off by rotary evaporation. TPE-Py was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 1:5) to obtain the solid yellow powder, otherwise TPE-Ph was eluted by petroleum ether/dichloromethane (1:2) to acquire the orange powder.

Statistics shows that 1,1,2,2-Tetrakis(4-bromophenyl)ethene is playing an increasingly important role. we look forward to future research findings about 61326-44-1.

Reference:
Article; Ma, Xiaoxie; Hu, Linli; Han, Xie; Yin, Jun; Chinese Chemical Letters; vol. 29; 10; (2018); p. 1489 – 1492;,
Bromide – Wikipedia,
bromide – Wiktionary