Author: Jessica.F

Electric Literature of 112279-72-8, 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. 112279-72-8 name is 4-Bromo-2,3-difluoroaniline, 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.

N-((4-bromo-2,3-difluorophenyl)carbamothioyl)benzamide was prepared according to the following procedure. To 4-bromo-2,3-difluoroaniline (3.70 g, 17.8 mmol) dissolved in acetone (20 mL) was added benzoyl isothiocyanate (2.90 g, 2.39 mL, 1 eq, 17.8 mmol) drop-wise. The reaction was stirred for 30 min at 18 C, the mixture was filtered, the collected white solid was washed with heptane (50 mL) and vacuum dried to afford N-((4-bromo-2,3-difluorophenyl)carbamothioyl)benzamide (5.68 g, 85%) as a white solid.?H NMR (300 MHz, DMSO-ifc) d 12.45 (s, 1H), 11.91 (s, 1H), 8.46 – 7.88 (m, 2H), 7.78 – 7.26 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,3-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; ACUCELA INC.; ORME, Mark, W.; ZUNIGA, Edison, S.; KUKSA, Vladimir, A.; CRAFT, Russell, Stuart; SAVEEDRA, Eduardo, Moreno; MEISSNER, Johannes, Wilhelm, Georg; DEN HARTOG, Jacobus, Antonius, Joseph; DROS, Albert, Cornelis; (223 pag.)WO2020/69330; (2020); A2;,
Bromide – Wikipedia,
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These common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, 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. COA of Formula: C6H11Br

General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to -78 C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 C. (Note 2:when the reaction mixture was heated at 30 C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 × 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. According to P1, 6-bromohex-1-ene (4s) (163 mg, 1.0 mmol) and s-BuMgCl (2g) (0.76 M in THF, 1.2 mmol) were reacted under standardconditions. After aqueous work-up, purification by GPC (withCHCl3 as the eluent) afforded the title compound.Yield: 120 mg (85%); pale yellow oil.IR (Zn/Se-ATR, neat): 2961, 2927, 2857, 1641, 1463, 1378, 991,910 cm-1.1H NMR (400 MHz, CDCl3): delta = 0.77 (d, J = 6.4 Hz, 3 H), 0.78 (t,J = 7.4 Hz, 3 H), 1.01-1.07 (br m, 2 H), 1.22-1.29 (br m, 7 H), 1.97(m, 2 H), 4.88 (dt, J = 10.1, 1.4 Hz, 1 H), 4.92 (dd, J = 17.2, 1.4 Hz,1 H), 5.74 (ddt, J = 17.2, 10.1, 6.9 Hz, 1 H).13C NMR (100 MHz, CDCl3): delta = 11.4, 19.2, 26.6, 29.3, 29.5, 33.9,34.3, 36.4, 114.1, 139.2.MS (EI): m/z (%) = 140 (39) [M]+, 125 (8), 111 (19).HRMS (EI): m/z [M]+ calcd for C10H20: 140.1565; found: 140.1561.

The synthetic route of 6-Bromo-1-hexene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iwasaki, Takanori; Takagawa, Hiroaki; Okamoto, Kanako; Singh, Surya Prakash; Kuniyasu, Hitoshi; Kambe, Nobuaki; Synthesis; vol. 46; 12; (2014); p. 1583 – 1592;,
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Application of 7745-91-7, 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. 7745-91-7 name is 3-Bromo-4-methylaniline, 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.

Example 46A N-(3-Bromo-4-methylphenyl)-3-tert-butylbenzamide 285 mg (1.53 mmol) of 3-bromo-4-methylaniline, 300 mg (1.68 mmol) of 3-tert-butylbenzoic acid and 698 mg (1.83 mmol) of HATU were dissolved in 3 ml of DMF, 0.32 ml (1.83 mmol) of N,N-diisopropylethylamine were added and the mixture was stirred at RT for 16 h. The reaction was then stirred into 20 ml of 0.1 M aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. Drying of the residue gave 490 mg (88% of theory) of the title compound. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 10.26 (s, 1H), 8.10 (d, 1H), 7.76 (d, 1H), 7.67 (dd, 1H), 7.63 (d, 1H), 7.46 (t, 1H), 7.33 (d, 1H), 2.33 (s, 3H), 1.34 (s, 9H). LC/MS (Method 3, ESIpos): Rt=1.35 min, m/z=347 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SUessMEIER, Frank; LOBELL, Mario; GRUeNEWALD, Sylvia; HAeRTER, Michael; BUCHMANN, Bernd; TELSER, Joachim; JOeRIssEN, Hannah; HEROULT, Melanie; KAHNERT, Antje; LUSTIG, Klemens; LINDNER, Niels; US2013/190290; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1647-26-3, The chemical industry reduces the impact on the environment during synthesis 1647-26-3, name is 1-Bromo-2-cyclohexylethane, I believe this compound will play a more active role in future production and life.

General procedure: The product from Example 32A (0.046 g, 0.2 mmol), 2-(bromomethyl)pyridine hydrobromide (0.066 g, 0.260 mmol), and potassium carbonate (0.069 g, 0.500 mmol) were combined in dimethylformamide (1.0 mL) and stirred for 16 hours. The reaction mix was partitioned between ethyl acetate and water. The organic layer was separated and concentrated. Purification by chromatography (silica gel, 0-4% methanol in dichloromethane) afforded the title compound (0.030 g, 46%). Example 42 was prepared according to the procedure of Example 40 substituting (2- bromoethyl)cyclohexane for 2-(bromomethyl)pyridine hydrobromide and heating the reaction mixture at 50 C for 6 hours. Purification by chromatography (silica gel, 0-100% ethyl acetate in hexane) afforded the title compound (0.038 g, 63%). 1H NMR (300 MHz, DMSO-d6) delta 7.35 – 7.45 (m, 1 H) 7.21 (dd, J=7.54, 1.59 Hz, 1 H) 7.07 (d, J=7.54 Hz, 1 H) 6.98 (t, J=7.93 Hz, 1 H) 6.36 (s, 1 H) 3.97 (t, J=6.35 Hz, 2 H) 3.71 (s, 3 H) 3.60 (s, 3 H) 1.56 – 1.67 (m, 5 H) 1.46 (q, J=6.61 Hz, 2 H) 1.03 – 1.36 (m, 4 H) 0.72 – 0.98 (m, J=l l .l l Hz, 2 H). MS (ESI+) m/z 343 (M+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-cyclohexylethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI)COMPANY, LTD.; HUBBARD, Robert Dale; MCDANIEL, Keith F.; PARK, Chang Hoon; PRATT, John K.; SOLTWEDEL, Todd; SUN, Chaohong; WANG, Le; WENDT, Michael D; WO2013/185284; (2013); A1;,
Bromide – Wikipedia,
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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. 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 452-63-1

Intermediate 2:; 4-Fluoro-2-methvl-benzaldehvde; 2-Bromo-5-fluorotoluene (15.0 g, 79.3 mmol) was dissolved in anhydrous THF andcooled to -78C in an acetone/dry ice bath. N-butyl-lithium (48.0 mL, 119 mmol) was addeddropwise down the side of the reaction flask and the resulting solution was stirred for 10 min. 64.0 ml of anhydrous DMF (793 mmol) was then added in the same fashion. After 1 hour, the reaction was quenched with cold aqueous NH4CI and diluted with 500 mL Et2O and washed with water (3x 300 mL)., The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude material was then equipped with a distillation apparatus and the oil bath was heated to 110 C. Product containing fractions were collected to give a colorless oil, (10.0 g , 72.4 mmol, 92% yield); LRMS m/z (APCI+) 139 [M+ H]; 400 MHz 1HNMR (CDCI3) 8 10.91 (s, 1H); 7.81 (dd, J=6.2, 2.5 Hz, 1H); 7.03 (ddd, J=8.2, 8.2, 2.5 Hz, 1H); 6.95 (ddd, J=9.5, 2.5, 0.0 Hz, 1H); 2.67 (s, 3H).

According to the analysis of related databases, 452-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/110996; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene, 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. name: 1-Bromo-2,4,5-trimethylbenzene

c. N,N,,N”,N”‘-(4,4,,4″,4,”-methanetetrayltetrakis(benzene-4, 1 – diyl))tetrakis(2,4,5-trimethyl-N-(2,4,5-trimethylphenyl)aniline) In a dry box, 4,4’,4″,4″‘-methanetetrayltetraaniline (1 .00 g, 3.08 mmol), 1 – bromo-2,4,5-trimethylbenzene (1 .35 g, 3.67 mmol), tris(tert- butyl)phosphine (0.1 0 g, 0.50 mmol) and Pd2(DBA)3 (0.23 g, 0.25 mmol) were combined in round bottom flask and dissolved in 120 ml of dry toluene. The solution was stirred for a minute and followed by sodium tert- butoxide (2.72 g, 28.33 mmol) and 5 ml of dry toluene. A heating mantle was added and the reaction heated to 80C for 18 hour. More 1 -bromo- 2,4,5-trimethylbenzene (350mg) and NaOtBu (180mg) were added and the reaction stirred at 80C for another 24 hour. The reaction mixture was then cooled to room temperature and filtered, washing with toluene (200 mL). The solvent was removed by rotary evaporation and the residue was re-dissolved in chloroform (40ml_). The crude product was precipitated into methanol (300ml_) and collected (3.3g, 85% pure) by filtration. The crude product was purified further by silica gel column chromatography using a gradient of chloroform in hexanes (5-21 %). Recrystallization from chloroform and ethanol yielded 2.60 g (64%) of product as a pale yellow solid. 1 H NMR (CDCI3) is consistent with structure for Compound 2.

The synthetic route of 1-Bromo-2,4,5-trimethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WANG, Ying; WU, Weishi; DOBBS, Kerwin, D.; WO2011/49904; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 766-46-1, The chemical industry reduces the impact on the environment during synthesis 766-46-1, name is 2′-Bromophenylacetylene, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

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, 2′-Bromophenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
Bromide – Wikipedia,
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Related Products of 3344-70-5, These common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, 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.

1.0 g of compound 3,2.63 g of 1,12-dibromododecane,0.43 g of potassium hydroxide and 0.16 g of tetrabutylammonium bromide,Was added to a mixture of 10 ml of dichloromethane and 6.5 ml of water,The mixture was stirred at room temperature under nitrogen for 24 hours,Washed twice with 30 ml of water,Washed once with 15 ml of saturated brine,The organic layer was separated,After adding anhydrous sodium sulfate to remove water,The solvent was removed on a rotary evaporator,(200: 300 mesh silica gel column chromatography elution (ethyl acetate / petroleum ether volume ratio of l: 30-l: 10),To give 1.19 g of the compound 4 as a pale yellow liquid,Yield 90percent.

Statistics shows that 1,12-Dibromododecane is playing an increasingly important role. we look forward to future research findings about 3344-70-5.

Reference:
Patent; Guilin University of Technology; Kong, Xiangfei; Dai, Shengping; Chang, Xiao; Zhang, Laiqi; Wang, Guixia; (10 pag.)CN106117220; (2016); A;,
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. name: 4-Bromo-2,6-difluoroaniline

Example 1 5-Bromo-1,3-difluoro-2-nitro-benzene: To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 m]L), stirred at 55 C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55 C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5*100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) delta 7.32 (dt, 2H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Charifson, Paul S.; Deininger, David D.; Grillot, Anne-Laure; Liao, Yusheng; Ronkin, Steven M.; Stamos, Dean; Perola, Emanuele; Wang, Tiansheng; LeTiran, Arnaud; Drumm, Joseph; US2005/256136; (2005); A1;,
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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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

To a solution of 4-bromo-3-fluoro-benzotrifluoride (585 mg, 2.36 mmol) in 15 mL of THF, stirred at -75 C. under nitrogen atmosphere, 1.53 mL (2.6 mmol) of a 1.7M solution of tert-butyllithium in pentane were added dropwise. The reaction mixture was stirred at -60 C. for 15 minutes then a solution of 2-methyl-propane-2-sulfinic acid-(tetrahydro-pyran-4-ylidene)-amide (400 mg, 1.97 mmol; prepared as described in literature: WO2005/87751 A2) in 10 mL of THF was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 1 hr. A saturated ammonium chloride solution was added and the reaction mixtures was extracted with ethyl acetate. The organic phases were collected, dried over sodium sulfate and concentrated under vacuum. The crude obtained was purified by flash chromatography (eluent: cyclohexane/AcOEt; gradient from 12% to 100% of AcOEt). The oil obtained was diluted in 2 mL of 1,4-dioxane, 0.4 mL of a 4 M solution of hydrochloric acid in 1,4-dioxane were added, the reaction mixture was stirred at room temperature for 1 hr and then concentrated under vacuum to obtain 100 mg of the title compound as white solid.LC-MS (Method 2): Rt=0.90 minMS (ESI pos): m/z=264 (M+H)+

The synthetic route of 40161-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; HOENKE, Christoph; BERTANI, Barbara; FERRARA, Marco; FOSSATI, Giacomo; FRATTINI, Sara; GIOVANNINI, Riccardo; HOBSON, Scott; (88 pag.)US2017/101411; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary