Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 118527-30-3, name is 2-Bromo-1,3-bis(trifluoromethyl)benzene, 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 118527-30-3, Application In Synthesis of 2-Bromo-1,3-bis(trifluoromethyl)benzene

General procedure: 12.6 g (38.32 mmol) of 9H-[3,9?]bicarbazolyl [18628-07-4], 7 g (38.32 mmol) of 2-bromo-1,3-ditrifluoromethylbenzene [118527-30-3] and 16 g of K2CO3are suspended in 300 mL of p-xylene. To the suspension are added 0.86 g (3.84 mmol) of Pd(OAc)2and 7.6 mL of a 1M tri-tert-butylphosphine solution. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, washed three times with 200 mL of water and then concentrated to dryness. The residue is subjected to hot extraction with toluene, recrystallized from toluene and finally sublimed under high vacuum. Yield: 14.5 g (35 mmol), 87% of theory; purity 99.9%

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; MerckPatent GMBH; Suttessel, Philip; Faram, AmirHossain; Blume, Christoph; Yatzi, Anya; (85 pag.)KR2015/132872; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 6274-57-3, A common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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: Pd(PPh3)4 (3 mol%) was added to a suspension of the appropriate benzoxazole 7 and (het)aryl bromide (1 equiv) in 1 M aq K2CO3 (3equiv) and 1,4-dioxane (0.15 M) at r.t. The mixture was stirred at reflux for 2 h then cooled to r.t. H2O was added, and the mixture was extracted with EtOAc. The organic layers were combined, washed with brine, dried (NaSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel,hexane-EtOAc or CHCl3-MeOH).

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; Fukaya, Takayuki; Masumoto, Shuji; Synthesis; vol. 45; 23; (2013); p. 3269 – 3275;,
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. 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. Formula: C7H3BrF4

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

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. SDS of cas: 2695-47-8

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;,
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. Application In Synthesis of 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;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 766-46-1, name is 2′-Bromophenylacetylene, 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 766-46-1, Product Details of 766-46-1

To a 10 mL screw cap vial, 2-bromophenylacetylene (0.5 mmol) and a solution of azidopentafluoroethane in THF (?0.60 mmol, 3-4 mL) were added. An aqueous solution of CuSO4-5H2O (1 mol·l-1, 0.05 mmol, 50 mul) and sodium L-ascorbate (1 mol·l-1, 0.05 mmol, 50 mul) were added, the vial was closed and the content was stirred at rt for 18 h. Saturated aqueous NH4Cl (10 mL) was added and the product was extracted into CH2Cl2 (3*10 mL). The combined organic phase was washed with water (2*10 mL), dried (MgSO4), filtered and solvent was removed under reduced pressure. Purification by column chromatography (silicagel) gave pure product as a white solid. Yield 37%; Rf (cyklohexane:EtOAc 95:5)=0.53; IR (CHCl3, film) v=1430, 1210, 1128, 1077, 972 cm; 1H NMR (400 MHz, CDCl3) delta=8.63 (s, 1H), 8.15 (dd, J=7.8, 1.7 Hz, 1H), 7.70 (dd, J=8.1, 1.2 Hz, 1H), 7.47 (td, J=7.6, 1.3 Hz, 1H), 7.29 (td, 1H); 13C NMR (101 MHz, CDCl3) delta=146.4, 133.9, 131.1, 130.6, 129.4, 128.1, 121.6, 121.4, 117.2 (qt, 1JC-F=287.5 Hz, 2JC-F=41.2 Hz, CF3), 110.3 (tq, 1JC-F=271.4 Hz, 1JC-F=43.2 Hz, CF2); 19F NMR (376 MHz, CDCl3) delta=-84.4 (s, 3F), -99.2 (s, 2F); HRMS (ESI) m/z calculated for C10H6N3BrF5 [M+H]+: 341.9660, found 341.9661.

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:
Patent; Ustav organicke chemie a biochemie AV CR, v.v.i.; CF Plus Chemicals s.r.o.; BEIER, Petr; MATOUSEK, Vaclav; BLASTIK, Zsofia E.; VOLTROVA, Svatava; (12 pag.)US2019/161452; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 927384-44-9, 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 927384-44-9 as follows.

Bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-benzene 11 (2.40 g, 7.43 mmol), 4-(ethoxycarbonyl)phenylboronicacid 12 (2.40 g, 12.4 mmol), powdered tripotassium phosphate(3.40 g, 20.7 mmol) and 1,4-dioxane (150 cm3) were added to around-bottom flask fitted with a condenser and heated at 80 Cfor 15 min under N2. Pd(PPh3)4 (0.47 g, 0.41 mmol) was added tothe mixture which was purged with N2 for a further 15 min beforebeing stirred at 80 C for 2 days. The mixture was allowed to cool,filtered and the filtrate concentrated under reduced pressure. Theresulting residue was dissolved in chloroform (100 cm3), washedwith water (3 x 50 cm3) and brine (50 cm3) and concentratedunder reduced pressure to give a brown solid, which wasrecrystallised from chloroform and methanol to give 13 as largeyellow needles (yield 2.07 g, 71%). 1H NMR (CDCl3, 400 MHz) delta 8.25-8.04 (m, 2H), 7.85-7.67 (m, 6 H), 7.19 (dd, J = 7.3, 8.2 Hz,2H), 7.11 (d, J = 7.8 Hz, 2H), 6.48 (dd, J = 0.8, 7.3 Hz, 2H), 6.11 (s,2 H), 4.45 (q, J = 7.2 Hz, 2H), 1.46 (t, J = 7.2 Hz, 3H). ESI-TOF-MS:m/z 392.23 [M]+. Elemental Anal. Calc. for C25H21BN2O2: C, 76.55;H, 5.40; N, 7.14. Found: C, 76.51; H, 5.33; N, 7.26%. ATR-FTIR(cm-1): 3360 (s), 2900 (m), 1590 (s), 1580 (s), 1360 (m), 1260(s), 1080 (m), 756 (m, br), 728 (m).

According to the analysis of related databases, 927384-44-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Argent, Stephen P.; Tarassova, Irina; Greenaway, Alex; Nowell, Harriot; Barnett, Sarah A.; Warren, Mark R.; Tang, Chiu C.; Morris, Christopher G.; Lewis, William; Champness, Neil R.; Schroeder, Martin; Blake, Alexander J.; Polyhedron; vol. 120; (2016); p. 18 – 29;,
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 64248-56-2 as follows. Recommanded Product: 2-Bromo-1,3-difluorobenzene

Preparation 105 Preparation of tert-Butyl 9-(2,6-difluorophenyl)-1,4,5,6-tetrahydroazepino-[4,5-b]indole-3(2H)-carboxylate. A solution of 1-bromo-2,6-difluorobenzene (0.28 g, 1.5 mmol) in dioxane (12 mL) was added to a flask charged with 3-(tert-butyloxycarbonyl)-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.50 g, 1.2 mmol), Pd2(dba)3 (0.11 g, 0.12 mmol) and potassium phosphate(0.59 g, 2.8 mmol). Next, trimethylphosphite (0.045 mL, 0.38 mmol) was added and the mixture was heated to 95 C. After 28.5 h, the reaction was cooled to rt, diluted with H2O, and extracted with EtOAc (3*50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M, SIM) with heptane/EtOAc (4:1) to give 0.38 g (80%) of a pale yellow solid: mp 225.5-226 C.; % water (KF): 0.10; melt solvate: 1.46% CH2Cl2; 0.19% EtOAc; Anal. Calcd for C23H24F2N2O2-0.10% H2O·1.46% CH2Cl2·0.19% EtOAc: C, 68.34; H, 6.19; N, 6.91; found: C, 68.34; H, 6.19; N, 6.81.

According to the analysis of related databases, 64248-56-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Frank, Kristine E.; Acker, Brad A.; Ennis, Michael D.; Fisher, Jed F.; Fu, Jian-min; Jacobsen, Eric Jon; McWhorter JR., William W.; Morris, Jeanette K.; Rogier, Donald Joseph; US2002/77318; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 445303-69-5,Some common heterocyclic compound, 445303-69-5, name is 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, molecular formula is C7H4BrF3, 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 4:4-[3-(DIFLUOROMETHYL)-4-FLUOROPHENYL]PYRIDINETo a mixture of 4-bromo-2-(diotafluoromethyl)-l-fluorobenzene (0.5 g, 2.24 mmol), 1- pyriotadyl-4-boroniotac acid (0.33 g, 2.69 mmol) and sodium carbonate (0.64 g, 5.6 mmol) in toluene/ethanol (1 : 1, 20 ml) under nitrogen, was added palladium tetrakis (0.13 g , 5 mol%). The mixture was heated at reflux for 16 h, cooled to ambient temperature and diluted with water (50 ml) and ethyl acetate (100 ml). The organic layer was separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases was evaporated to dryness and dissolved in aqueous hydrochloric acid (10%, 50 ml). The solution was washed with diethyl ether (2×40 ml), basified with aqueous sodium hydroxide (2M) and extracted with ethyl acetate (2×50 ml). The combined organic phases was dried (MgSO4) and evaporated to dryness to give the crude product. Purification by flash column chromatography (ethyl acetate/isooctane 2: 1) gave the title compound (0.34 g). MS m/z (rel. intensity, 70 eV) 223 (M+, bp), 222 (12), 204 (7), 172 (12), 145 (8).

The synthetic route of 445303-69-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; A. CARLSSON RESEARCH AB; WO2007/65655; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 626-40-4,Some common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, molecular formula is C6H5Br2N, 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 of the compound 3-((3-cyano-6-cyclopropylpyridin-2-yl)thio)-N-(3,5-dibromophenyl)propanamide (19) I-3 (0.50) g, 2 mmol, 1 eq), EDCI (0.50 g, 2.6 mmol, 1.3 eq) and HOBT (0.08 g, 0.6 mmol, 0.3 eq) dissolved in DMF, not more than 10 C, The reaction was carried out for 30 min, and 3,5-dibromoaniline (0.56 g, 2.2 mmol, 1.1 eq) was added. the color of the reaction solution was darkened and reacted overnight at room temperature. The reaction was complete by TLC. Post-treatment: The reaction solution was poured into water, suction-filtered, and then filtered to give a crude product. The crude product was recrystallized from petroleum ether-ethyl acetate to afford LWTW-225 (150 mg, yield 31%).

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

Reference:
Patent; Yao Da Pharmaceutical Co., Ltd.; Bian Jinlei; Zhao Lulu; Wang Jubo; Ma Yinghe; Li Zhiyu; (15 pag.)CN109574920; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary