Bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 7766-50-9, name is 11-Bromo-1-undecene, 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 7766-50-9, 7766-50-9

The absolute configuration of acetates 5 and 6 was confirmed by alternative chiral synthesis of (2S’,122)-2-acetoxy-12-heptadecene (6) using hydrolytic kinetic resolu- tion (HKR) as the key step (FIG. 6), as follows: 37.5 mmol of butyl lithium (15 ml of 2.5 M solution in hexane) was added under argon at -700C to 3.45 ml (30.0 mmol) of 1-hexyne (9) in 50 ml THF. After stirring 0.5 hours, 5 ml of HMPA and 1.8 ml (8.20 mmol) of 11-bromo-l-undecene (10) was added. The reaction mixture was then warmed to room temperature, stirred 24 hours, quenched with aq. NH4Cl, and extracted with hexane (2 x 50 ml). Combined extracts were washed with brine, dried (anh. MgSO4), and solvents evaporated. The crude product was filtered through 10 g of silica eluting with hexane, yielding 2.05 g of hydrocarbon 11 (85% pure by GC; 7.65 mmol). Without further purification compound 11 was treated with 13.1 mmol of r¡ã-chloroperoxybenzoic acid at 0C in 20 ml of dichloromethane. After 3 hours, the mixture was warmed to room temperature, and after a subsequent 30 min quenched with 50 ml of 2N NaOH and treated with 100 ml of ether. The organic layer was separated, washed with water and brine, and dried (anh. MgSO4). After filtration, removal of solvents in vacuo and flash chromatography, 0.82 g (87% pure by GC; 2.85 mmol) of unsaturated epoxide 12 was obtained. Epoxide 12 in 3 ml of dry THF with 0.030 ml of water was subjected to HKR with freshly prepared R,R-1 Jacobsen catalyst (7,8) [25 mg of (R,R)-N,NN -bis(3 ,5-di-tert-butylsalicylidene)-l ,2-cyclohexanediaminocobalt(II) (Aldrich Chemical Company, Milwaukee, WI) stirred 1 hour with 0.20 ml of toluene and 0.050 ml of acetic acid, and solvents removed in vacuo]. After stirring the reaction mixture 7 days, the recovered (R)-epoxide 13 was separated by flash chromatography [15 g of silica with hexanerether (80:20) as eluent] from the diol 14 and the catalyst, affording 0.4 g of 85% pure (R)-epoxide 13. After removal of solvents, 13 was dissolved in 2 ml of ether and added to a lithium aluminum hydride suspension (10 mmol) in 20 ml of ether. After stirring 3 hours, the reaction mixture was quenched with 2nu NaOH, and the organic phase removed and evaporated. The resulting acetylenic alcohol 15 was hydrogenated in 30 ml of hexane with Lindlar catalyst (5% palladium on calcium carbonate poisoned with lead, 100 mg) and 1 ml of quinoline, yielding 0.350 g of (25′,12Z)-2-hydroxy-12-heptadecene (4). Acetylation of 4, as described above, and further flash column purification gave 0.350 g (1.18 mmol) of (25,12Z)-2-acetoxy-12-heptadecene (6) (yield 14.5% based on 11-bromo-l-undecene 10) with 85% ee.

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, 11-Bromo-1-undecene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRIES, Regine; KHASKIN, Grigori; DAROOGHEH, Hassan; MART, Cafer; BRITTON, Robert; GRIES, Gerhard; WO2007/79563; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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 327-52-6, 327-52-6

Example 1: Preparation of (S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol (formula 4) [Show Image] Preparation of 2,4,5-trifluorophenylmagnesium chloride solution: 700 mL of tetrahydrofuran was charged into reactor and cooled to 0 C, followed by the consecutive addition of 350 mL 2 M i-propylmagnesium chloride and 69 mL 1-bromo-2,4,5-trifluorobenzene applying stirring and maintaining temperature of the reaction mixture between 0 C and 5 C. After the addition, the reaction mixture was stirred gently for 1 h at 0 C to 5 C and for 3 h at 22 C obtaining the solution of 2,4,5-trifluorophenylmagnesium chloride.Determination of activity of the obtained solution: 0.25 g of iodine was weighed into small reaction flask and titrated with the solution obtained. When darkly brown solution turned its color to white suspension, the consumption of solution was ready. Typical consumption was about 1.85 mL/mmol of iodine.Conversion to compound of formula 4: To the whole amount of above prepared solution of Grignard reagent 28 mL of (S)-epichlorohidrin (formula 3) was added during stirring, followed by the addition of 0.80 g copper(I) chloride. Exotermic reaction started and when inner temperature raised to 40 C, external cooling was applied, lowering the internal temperature to 25 C. 28 mL of (S)-epichlorohidrin divided into two equal portions were added. After the addition, the reaction mixture was stirred for 5 h at 25 C, followed by the addition of 75 mL acetic acid and 750 mL methyl tert-butyl ether. The resulted mixture was washed consecutively with 700 mL water; mixture of 700 mL water, 80 mL brine, 80 mL 20% ammonium chloride, and 750 mL 2% sodium bicarbonate. Organic phase was evaporated at 60 C and 5 mbar, to yield 131 g of crude product of compound of formula 4 in the form of yellowish oil. 1H NMR (DMSO-d6): delta 2.64 (dd, 1H), 2.83 (dd, 1H), 3.49-3.64 (m, 2H), 3.85 3.90 (m,1H), 5.31 (d,1H), 7.37-7.48 (m, 2H).

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-2,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2397141; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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. 4549-33-1

n-BuLi (1.63 M in hexane, 4.0 mL, 6.52 mmol) was added to a solution of iPr2NH (0.62 mL, 4.4 mmol) in tetrahydrofuran (THF) (5 mL) at 0C, and the whole mixture was stirred for 30 min at 0C. 3-Picoline (0.39 mL, 4.02 mmol) was added to the mixture at -78C, and the whole mixture was stirred for 20 min. Then, 1,9-dibromononane (2.43 mL, 12 mmol) was added to the mixture, and the whole mixture was gradually warmed to r.t. with stirring overnight. Sat. NaHCO3aq. was added to the reaction mixture, and the whole mixture was extracted with AcOEt. The combined organic layer was washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure to give a crude product, which was purified by SiO2 column chromatography (hexane-AcOEt=8 : 1) to give 5b(388 mg, 33%).1H-NMR (500 MHz, CDCl3) delta: 8.35-8.30 (2H, m), 7.39 (1H, d, J=7.7 Hz), 7.10 (1H, dd, J=7.7, 4.9 Hz), 3.30 (2H, t, J=6.9 Hz), 2.50 (2H, t, J=7.7 Hz), 1.74 (1H, quint, J=7.1 Hz), 1.53-1.48 (2H, m), 1.35-1.12 (12H, m). 13C-NMR (125 MHz, CDCl3) delta: 149.6, 146.8, 137.6, 135.5, 123.0, 33.8, 32.7, 32.5, 30.8, 29.11, 29.10, 29.07, 28.8, 28.4, 27.9. IR (KBr) cm-1: 2926, 2854, 1574, 1422, 1026. ESI-TOF-MS m/z: 298 (M+H)+. HRESI-TOF-MS m/z: 298.1163 (Calcd for C15H25NBr: 298.1170).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4549-33-1, its application will become more common.

Reference:
Article; Arai, Masayoshi; Kamiya, Kentaro; Shin, Dayoung; Matsumoto, Hirokazu; Hisa, Tomoya; Setiawan, Andi; Kotoku, Naoyuki; Kobayashi, Motomasa; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 766 – 771;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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. 1647-23-0

The first step, weighed indole acetic acid (1.05g),Added to DMF (5 mL) and stirred to dissolve,Cooling to 0 ~ 5 C stirring;60% sodium hydride (0.72 g) was added,Stirring for 10min,3,3-dimethyl-1-bromobutane(1.5 g) was added,0 ~ 5 C reaction 0.5h,Slowly rose to room temperature reaction 2h;Add ethyl acetate (40mL), water (40mL); rapid mixing, 2min drop 6N hydrochloric acid solution 10mL,Stirring for 5 min; the phases were separated and the aqueous phase was extracted with ethyl acetate (20 mL). The phases were separated and the ethyl acetate phases were combined. Saturated brine(30 mL) for 5 min,The ethyl acetate phase was removed at 50 C under reduced pressure to give the crude product of the first step2- [1- (2-tert-butylethyl) -1H-indol-3-yl] acetic acid.

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 1647-23-0.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Shi Jiangong; Guo Ying; Xu Chengbo; Chen Qing; Chen Minghua; Ba Mingyu; Zhu Chenggen; Tang Ke; Jiang Jiandong; Guo Jiamei; Guo Qinglan; Lin Sheng; Yang Yongchun; (44 pag.)CN107151223; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, Adding some certain compound to certain chemical reactions, such as: 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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 40161-54-4.

Example 42: N-(5-Fluorothiazol-2-yl)-5-(2-(4-methylpiperazin-l-yl)-4- (trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide Step 1 : 5-(2-(4-Methyl-lH-imidazol-l-yl)-4-(trifluoromethyl)phenyl)isoquinoline A suspension of sodium hydride 60% (0.330 g, 13.75 mmol) in 8 mL DMF was cooled to 0 C and was treated with 4-methyl-lH-imidazole (0.676 g, 8.23 mmol). After stirring for 40 minutes, l-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.180 ml, 8.23 mmol) was added, and the reaction mixture was heated to 120 C for 90 minutes. At this point Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, MO, 0.291 g, 0.412 mmol), isoquinolin-5- ylboronic acid (1.424 g, 8.23 mmol), potassium phosphate (6.99 g, 32.9 mmol), 16 mL dioxane and 12 mL water were added, and the reaction mixture was heated to 120 C overnight. The reaction mixture was poured into saturated aHC03 solution and was extracted with DCM. The organics were concentrated then purified by reverse phase column chromatography [RediSep Gold C18 150g, 15 to 100% (0.1% NH40H in MeOH)/(0.1% NH40H in water)] yielding 5-(2-(4-methyl-lH-imidazol-l-yl)-4- (trifluoromethyl)phenyl)isoquinoline (1.435 g, 4.06 mmol) as an about 4: 1 mixture of isomers.

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 40161-54-4.

Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); 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. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2606-51-1

General procedure: The mixture of N-hydroxyhept-6-ynamide (141 mg, 1 mmol), benzyl bromide (256 mg, 1.5 mmol), sodium azide (98 mg, 1.5 mmol), copper(II) sulfate pentahydrate (38 mg, 0.13 mmol), sodium ascorbate (60 mg, 0.3 mmol) in wate and tert-butanol (v/v = 1:1, 10ml) was heated to 66 oC, the heterogeneous mixture was stirred vigrously for 24 h. After addition of water (50 ml), the mixture was filtered. The filter cake was dissloved in MeOH (20 ml), the insolubles was filtered, the filtrate was concentrated in vacuo and crystallized in ethyl acetate to give 2 (156 mg, 57%) as a white solid.

The synthetic route of 2606-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Qiao; Yao, Yiwu; Liu, Chunping; Li, Hua; Yao, Hequan; Xue, Xiaowen; Liu, Jinsong; Tu, Zhengchao; Jiang, Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3295 – 3299;,
Bromide – Wikipedia,
bromide – Wiktionary

5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows.

TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE: was prepared from 3-bromopropylamine hydrobromide and BOC2O in the presence of base in dichloromethane.

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; Synaptic Pharmaceutical Corporation; US6727264; (2004); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, 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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below.

General procedure: Benzimidazole (5 mmol), 1-bromo-2-fluorobenzene derivatives (15 mmol, 2 equiv) and tripottasium phosphate (5.31g, 25 mmol, 5 equiv) were dissolved in DMF (30 mL). The mixture was stirred at 150 C. The reaction time was determined by monitoring with TLC. The reaction mixture was diluted with CH2Cl2 (50 mL) and water (50 mL). The phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 ¡Á 30 mL). The combined organic layerswere washed with water (3 ¡Á 50 mL), dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/AcOEt).

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:
Article; Matsumura, Mio; Kitamura, Yuki; Yamauchi, Arisa; Kanazawa, Yoshitaka; Murata, Yuki; Hyodo, Tadashi; Yamaguchi, Kentaro; Yasuike, Shuji; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2029 – 2035;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, name is 3-Bromo-2-methylaniline, 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. 55289-36-6

To a solution of 10.0 g (53.7 mmol, 1.0 eq.) of 3-bromo-2-methylamine (LXXXVIIa) in 200 mL of acetonitrile at 0 C was added 42 mL of cone. HC1 followed by 42 mL of glacial acetic acid and a solution of 4.4 g (63.9 mmol, 1.1 eq.) of sodium nitrite in 12 mL of water. The mixture was purged with SO2 gas for 15 mm and a solution of 9.1 g (53.7 mmol, 1.0 eq.) ofcopper (II) chloride in 12 mL of water was added dropwise at 0 C. The mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was concentrated in vacuo, diluted with 500 mL of water and extracted with 3 x 500 mL of ethyl acetate. The combined organic extracts were washed with 200 mL of sat. aqueous sodium bicarbonate solution, 200 mL of brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue waspurified by trituration with pentane to provide 8.0 g (29.7 mmol, 55%) of 3-bromo-2- methylbenzene-1-sulfonyl chloride (LXXXVIIIa). ?H NIVIR (400 MFIz, CDC13): 8.07 (d, 1H), 7.92 (d, 1H), 7.28 (t, 1H), 2.88 (s, 3H).

Statistics shows that 55289-36-6 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-methylaniline.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5,Some common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, molecular formula is C6H3BrF2, 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-(19): 1-(2,3-Difluorophenyl)-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone Isopropylmagnesiumchloride-LiCl complex (1.30 M in THF, 155.0 mL, 0.0715 mol) under nitrogen was cooled to 0-5¡ã C., and 2,3-difluorobromobenzene (13.8 g, 0.0715 mol, 1.50 equiv.) was added while T<10¡ã C. After 1 h at 0-5¡ã C., a solution of 1-morpholino-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone (21.8 g, 0.048 mol, 1.0 equiv.) in THF (2.0 vols) was added while T<10¡ã C. The reaction mixture was stirred for 2.5 h and monitored for consumption of 1-morpholino-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone (target>97percent). The reaction mixture was quenched by charging into cold sat. aq. NH4Cl (110 mL) and water (33 mL) while T<20¡ã C. 2-Methoxy-2-methylpropane (218 mL) was added and the layers were separated. The organics were washed with sat. aq. NH4Cl (65 mL) and 18percent aq. NaCl (44 mL). The organics were concentrated under vacuum T<25¡ã C. to a light yellow oil (21.6 g). 1H NMR (500 MHz, CDCl3) delta ppm 7.70-7.64 (m, 1H), 7.47-7.42 (m, 6H), 7.37-7.30 (m, 1H), 7.30-7.25 (m, 6H), 7.24-7.19 (m, 3H), 7.19-7.13 (m, 1H), 5.84-5.71 (m, 1H), 5.30 (d, J=17.3 Hz, 1H), 5.25 (d, J=10.4 Hz, 1H), 4.78 (dd, J=17.7, 3.1 Hz, 1H), 4.70 (dd, J=17.7, 3.1 Hz, 1H), 4.03 (dd, J=11.8, 6.5 Hz, 1H), 3.35 (dd, 1=9.8, 6.4 Hz, 1H), 3.18 (dd, J=9.8, 4.6 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta ppm 194.15 (dd, JCF=4.9, 2.4 Hz), 150.77 (dd, JCF=250.3, 14.1 Hz), 150.29 (dd, JCF=256.4, 13.9 Hz), 143.98, 135.34, 128.75, 127.76, 126.95, 125.70 (d, JCF=12.0 Hz), 125.16 (d, JCF=3.5 Hz), 124.55 (dd, JCF=6.4, 4.2 Hz), 121.62 (d, JCF=17.6 Hz), 118.83, 86.78, 81.35, 74.98 (d, JCF=9.5 Hz), 66.71. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38573-88-5, its application will become more common. Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Takaishi, Mamoru; Ishida, Tasuku; US2014/179690; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary