Tag: M.W=200-300

33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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: 5-Bromo-2,2-difluorobenzodioxole

Example 1 : 3-(2,2-Difluoro-benzo[1 ,31dioxol-5-ylmethyl)-piperidine-1 -carboxylic acid pyridin-3-ylannide.Step A: 3-(2,2-Difluoro-benzo[1.SIdioxol-delta-ylnnethvD-piperidine-i-carboxylic acid tert-butyl ester.; 1 -Boc-3-methylene piperidine (842 mg, 4.27 mmol) was degassed (neat) for 15 minutes and then treated with a THF solution of 9-BBN (0.5 M in THF, 8.6 ml_, 4.3 mmol). The reaction mixture was refluxed for 2 h, then cooled to rt. The reaction mixture was then added, via cannula, to a preformed solution of 5-bromo-2,2-difluoro-1 ,3-benzodioxole (1.00 g, 4.22 mmol), Pd(dppf)CI2?CH2CI2 (94 mg, 0.128 mmol), and potassium carbonate (746 mg, 5.40 mmol) in DMF/H2O (10 mL/1 ml_). The resultant mixture was heated at 60 0C for 18 h, cooled to rt, poured into water, basified to pH 11 with 1 N NaOH, and extracted with EtOAc (3x). The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give 3-(2,2-difluoro-benzo[1 ,3]dioxol-5-ylmethyl)- piperidine-1 -carboxylic acid tert-butyl ester (1.00 g, 67%).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68452; (2010); A1;,
Bromide – Wikipedia,
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Application of 2635-13-4, 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 2635-13-4 as follows.

201mg (1mmol) of 3,4-methylenedioxybromobenzene, 1mL aqueous ammonia (25-28%, 13.3mmol), 8mg (0.1mmol) CuO, 79mg (0.2mmol) diethylenetriaminepentaacetic acid, 112mg ( 2mmol) KOH, 1mL H2O was added 10mL reaction tube, sealed and reacted at 100C for 12h. After the reaction was stopped, extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, purified by silica gel column chromatography purification, in 3,4-methylenedioxyaniline 100mg, The yield was 73%.

According to the analysis of related databases, 2635-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-Sen University; ZHU, XIN HAI; YANG, BO; LIAO, LI HAO; CENG, YONG HENG; WAN, YI QIAN; (9 pag.)CN103739417; (2016); B;,
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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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-N,N-dimethylaniline

a) Synthesis of2-(bis(3-(dimethylamino)phenyl)(hydroxy)methyl)phenol Phenyllithium (2 M in cyclohexane, 9.86 mL, 19.7 mmol) was added during 15 min to a solution of methyl salicylate (3.00 g, 19.7 mmol) in tetrahydrofuran (THF, 20 mL) at -78¡ãC. After stirring for 5 min at -78¡ãC, the reaction mixture was transferred during 20 min to a Grignard reagent prepared from 3-bromo-N,N-dimethylaniline (7.89 g, 39.4 mmol) and magnesium turnings (1.15 g, 47.3 mmol) in THF (ca. l lO mL), which was maintained at 0¡ãC during the addition. The reaction mixture was left warming to room temperature. After stirring at room temperature for 24 h, the reaction mixture was decanted and quenched with a saturated solution of ammonium chloride (ca. 200 mL). Extraction with ethyl acetate, drying (Na2S04) and concentrating gave 7.97 g of the crude product. Column chromatography (Si02, heptane/ethyl acetate 3: 1) finally yielded 2.15 g (30percent) of the target compound. 1H-NMR: 7.20-7.12 (m, 3 H), 6.88-6.84 (m, 1 H), 6.74-6.70 (m, 1 H), 6.70-6.65 (m, 4 H), 6.64-6.60 (m, 1 H), 6.53-6.48 (m, 2 H), 3.70 (br. s, 1 H), 2.84 (s, 12 H). 13C-NMR: 156.25, 150.35, 145.92, 130.37, 130.18, 129.23, 128.60, 118.77, 117.30, 116.58, 112.36, 112.01, 85.01, 40.59.

The synthetic route of 16518-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FIRMENICH SA; HERRMANN, Andreas; (36 pag.)WO2016/116420; (2016); A1;,
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Synthetic Route of 86845-27-4, 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 86845-27-4 as follows.

(44-1) After N-bromosuccinimide (1.49 g, 6.63 mmol) and 2,2′-azobis(isbutyronitrile) (20 mg) were added to a solution of 4-bromo-1-methyl-2-(trifluoromethyl)benzene (2.0 g, 8.4 mmol) in carbon tetrachloride (20 ml), the mixture was heated under reflux for 5 hours. The temperature of the reaction mixture was returned to room temperature and the residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluding solvent: n-hexane) to give crude 4-bromo-1-bromomethyl-2-(trifluoromethyl)benzene.

According to the analysis of related databases, 86845-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1806332; (2007); A1;,
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Electric Literature of 33070-32-5, 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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 29 4-(2,2-difluoro-13-benzodioxol-5-yl)-2-fluoroaniline A solution of 5-bromo-2,2-difluoro-1,3-benzodioxole (1.73 mmol), bis(pinacolato)diboron (1.90 mmol), potassium acetate (5.20 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)¡¤dichloromethane adduct (0.32 mmol) in N,N-dimethylformamide (8.0 mL) was heated at 80 C. for 2 h. The reaction mixture was cooled and was treated with 2-fluoro-4-iodoaniline (0.86 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)¡¤dichloromethane adduct (0.32 mmol), cesium carbonate (8.65 mmol), and water (2.0 mL). The reaction mixture was then heated at 100 C. for 18 h. The reaction mixture was cooled, poured into brine (60 mL), and extracted with (3*50 mL) ethyl acetate. The combined organic layers were dried over magnesium sulfate and decolorizing charcoal, filtered through Celite, and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC and neutralization of the collected fractions afforded the title product as a tan solid (70%). ESMS [M+H]+: 267.8.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2,2-difluorobenzodioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; CYTOKINETICS; US2007/259951; (2007); 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H13Br

It was prepared as outlined in Scheme 1. In an oven-dried 50 mL round bottom flask under an atmosphere of anhydrous argon, THF (10 mL) was added followed by 1-bromo-3-tert-butylbenzene (5.00 mmol, 1.07 g). This clear, colourless solution was cooled to -90 ¡ãC using a Juablo cooler with a cold finger and an isopropanol bath in an appropriate sized Dewar. This solution was stirred at this temperature for 15 min to ensure it was sufficiently cold. Butyl lithium (3.44 mL, 1.60 M in hexanes) was added dropwise at -90 ¡ãC over 20 min. The resulting clear light yellow solution was stirred for 15 min at -90 ¡ãC. N-Methoxy-N-methyl-2-chloro-2,2-difluoroacetamide (5) (5.50 mmol, 1.00 g), described below, was dissolved in anhydrous THF (4 mL) then added dropwise to the cooled solution of the 1-lithium 3-tert-butylphenyl intermediate over 15 min. The resulting solution was stirred at -90 ¡ãC for 30 min then warmed to room temperature by removing the reaction flask from the cooling bath. The resulting reaction mixture was stirred for 16 h at room temperature then quenched with 1 M HCl (20 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (3 * 10 mL). The combined organic layers were dried over Na2SO4, gravity filtered and concentrated in vacuo. The crude viscous clear liquid was purified by flash chromatography on silica gel (10percent ethyl acetate/90percent hexanes, Rf: 0.40) to yield the desired product as a clear, colourless liquid (0.629 g, 51percent). 1H NMR (CDCl3): d1.37 (s, 9H), 7.46 (t, J = 7.9 Hz,1H), 7.71?7.75 (m, 1H), 7.92?7.95 (m, 1H), 8.16 (br s, 1H) (SupplementaryFig. S19). 13C NMR (CDCl3): d 31.1, 35.0, 120.3 (t, JC,F = 305.1 Hz), 127.5, 127.8 (t, JC,F = 3.2 Hz), 128.6, 129.2, 132.5, 152.2, 181.5 (t, JC,F = 28.2 Hz) (Supplementary Fig. S20). IR (Neat):3410 (w), 3072 (m), 2964 (s), 2871 (s), 1713 (s), 1599 (s), 1579(s), 1367(s), 1162 (s) cm1 (Supplementary Fig. S21). LRMS m/z:248 (M+2, 2percent), 247 (M+1, 1percent), 246 (M+, 5percent), 233 (17percent), 231 (50percent), 203 (22percent), 162 (13percent), 161 (100percent), 145 (11percent), 118 (12percent), 117(10percent), 115 (10percent), 91 (11percent) (Supplementary Fig. S22). HRMS (ESI): MNa+ found 269.0524, calcd for C12H13ClF2ONa+ = 269.0515 (SupplementaryFig. S23). HPLC: Retention time 2.33 min; purity98percent (Supplementary Fig. S24).

The synthetic route of 3972-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jollymore-Hughes, Courtney T.; Pottie, Ian R.; Martin, Earl; Rosenberry, Terrone L.; Darvesh, Sultan; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5270 – 5279;,
Bromide – Wikipedia,
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Reference of 25462-61-7, These common heterocyclic compound, 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine, 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.

In a Schlenk flask, 2,5-dibromo-1,4-phenylenediamine (500 mg, 1.88 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yI)-5-hexylthiophene 13 (2.21 g, 7.52 mmol)were charged under the protection of nitrogen. After adding 25 ml toluene, 10 mlethanol and 10 ml Cs2CO3 aqueous solution (2.0 mo/l), the mixture was degassedfor 30 mm. Pd(PPh3)4 (217.3 mg, 18.8 mmol) was added, then the mixture washeated to 80 C and stirred overnight. The reactant was poured into brine andextracted by dichloromethane for several times. The organic phase was dried overMg2504 and the solvent was evaporated in vacuo. The product was purified bychromatography on silica gel (petroleum ether/CH2CI2=1) to give product 14 asyellow flaky crystal (550 mg, 66%). 1H NMR (400 MHz, CDCI3, ppm): 0.90 (t, J = 7.02Hz, 6H), 1.46-1.23 (m, 12H), 1.76-1.64 (m, 4H), 2.82 (t, J = 7.65 Hz, 4H), 3.70 (br,4H), 6.79-6.73 (m, 4H), 7.02 (d, J 3.48 Hz, 2H). m/z[M+HJ calcd for C26H37N2S2441.2399; HR-ESI observed 441.2393. 13C NMR (100 MHz, CDCl3, ppm): 149.5,146.0, 133.3, 129.4, 128.9, 128.4, 122.2, 112.9, 32.0, 31.9, 30.7, 29.1, 22.8, 14.3.

The synthetic route of 25462-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; ZHANG, Fan; WANG, Xinyang; TANG, Ruizhi; FU, Yubin; ZHUANG, Xiaodong; FENG, Xinliang; WU, Dongqing; WO2015/43722; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 33070-32-5, The chemical industry reduces the impact on the environment during synthesis 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, I believe this compound will play a more active role in future production and life.

A solution of 5-bromo-2,2-difluoro-1 ,3-benzodioxole (1.73 mmol), bis(pinacolato)diboron (1.90 mmol), potassium acetate (5.20 mmol), and dichloro[1 ,1′- bis(diphenylphosphino)ferrocene]palladium(ll)?dichloromethane adduct (0.32 mmol) in Lambda/,Lambda/-dimethylformamide (8.0 ml_) was heated at 80 0C for 2 h. The reaction mixture was cooled and was treated with 2-fluoro-4-iodoaniline (0.86 mmol), dichloro[1 ,1 ‘- bis(diphenylphosphino)ferrocene]palladium(ll)?dichloromethane adduct (0.32 mmol), cesium carbonate (8.65 mmol), and water (2.0 mL). The reaction mixture was then heated at 100 0C for 18 h. The reaction mixture was cooled, poured into brine (60 mL), and extracted with (3 x 50 ml.) ethyl acetate. The combined organic layers were dried over magnesium sulfate and decolorizing charcoal, filtered through Celite, and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC and neutralization of the collected fractions afforded the title product as a tan solid (70%). ESMS [M+H]+: 267.8.

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, 5-Bromo-2,2-difluorobenzodioxole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; CYTOKINETICS; WO2006/20358; (2006); A2;,
Bromide – Wikipedia,
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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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

500ml round bottom flask reactor, 1-bromodibenzofuran(20.0g, 0.081mmol), bis(pinacolato)diboron (26.7g, 0.105mol), [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (1.3g, 0.002mol), potassium acetate (19.9g, 0.202mol), into a 1,4-dioxane 200ml were stirred for 10 hours under reflux after completion of the reaction was filtered a pad of celite. Filtrate was concentrated under a reduced pressure was separated and then the column was recrystallized from dichloromethane and heptane to give a intermediate 4-a> (17.0g, 70%).

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:
Patent; SFC CO LTD; PARK, SEOK BAE; SONG, JU MAN; LEE, YUR IM; KIM, HEE DAE; PARK, SANG WOO; JEONG, KYUNG SEOK; CHA, SOON WOOK; (96 pag.)KR2015/130206; (2015); A;,
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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. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., SDS of cas: 337915-79-4

Step C6-bromo- 1 -methyl- 1 H-benzimidazol-2-[00304] A solution of (2-amino-5-bromophenyl)methylamine (992 mg, 4.93 mmol) inMeOH (10 mL) was treated with cyanogen bromine (1045 mg, 9.87 mmol). The reaction mixture was maintained at room temperature for 1 h, then partitioned between EtOAc (100 mL), a sat. NaHC03 solution (100 mL) and water (20 mL). The organic layer was washed with a sat. NaCI solution, dried (Na2S04) and concentrated. The residue was triturated using CH2CI2 to obtain 6- bromo-1-methyl-1 H-benzimidazol-2-amine (952 mg, 4.21 mmol, 85 % yield) as a beige solid:.1H NMR (400 MHz, DMSO-cfe) delta ppm 3.48 (s, 3 H) 6.57 (s, 2 H) 7.04 (d, J=0.98 Hz, 2 H) 7.30 – 7.38 (m, 1 H) ES LC-MS m/z =226.1 (Br79, M+H)+; ES LC-MS m/z =228.1 (Br81, M+H)+.

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:
Patent; GLAXOSMITHKLINE LLC; BOTYANSZKI, Janos; DICKERSON, Scott Howard; LEIVERS, Martin Robert; LI, Xiaofei; MCFADYEN, Robert Blount; REDMAN, Aniko Maria; SHOTWELL, John Bradford; XUE, Jianjun; WO2012/174312; (2012); A2;,
Bromide – Wikipedia,
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