Tag: M.W=100-200

Some common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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. Application In Synthesis of 1-Bromo-3-fluorobenzene

A nitrogen-protected four-necked flask was charged with 268 g of diisopropylamine and 100 g of tetrahydrofuran, cooled to -40 C to -50 C, and 340 g was added dropwise at -40 C to -50 C Butyl lithium, stirring and holding 1 hour, the raw material reaction is completed. Cooling to -70 ~ -80 ,A mixture of 200 g of fluorobromobenzene and 100 g of tetrahydrofuran was added dropwise,Stir for 2 hours. After the addition of dimethylformamide 112 g, stirring for 1 hour, hydrochloric acid quenching pH = 1 ~ 2.The ethyl acetate extract was distilled under vacuum under reduced pressure to give 165 g of 2-fluoro-6-bromobenzaldehyde and 98% pure GC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1073-06-9, its application will become more common.

Reference:
Patent; Dalian Lianhua Chemical Co., Ltd.; Liu Qibin; Wang Zhongxing; (5 pag.)CN106977535; (2017); A;,
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630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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. Recommanded Product: 1-Bromo-2,2-dimethylpropane

l-(2,2-dimethylpropyI)-4-fluoro-S-methoxy-3-met yl-l,3-dihydro-2H-benzimidazol~2-one (7-5)A solution of 7-fluoro-6-methoxy-l -methyl- 1 ,3 -dihydro-2H-benzimidazol-2-one (7-4, 250 mg, 1.27 mmol) in anhydrous DMF (1.5 ml) was treated with NaH and l-Bromo-2,2- dimethylpropane. The reaction was then irradiated in a microwave at 175 deg C for 25 min. The reaction was partitioned between EtOAc (2×60 ml) and water (75 ml). The combined organic layers were dried over Na2S04 and concentrated, affording the title compound, 1 -(2,2- dimethylpropyl)-4-fluoro-5-methoxy-3-methyl-l,3-dihydro-2H-benzimidazol-2-one (7-5), as an orange oil. 1HNMR (300 MHz, CDC13) delta 6.65-6.70 (m, 2H), 3.88 (s, 3H), 3.60 (m, 5H)} 1.03 (s, 9H). LRMS m/z Calc’d for Ci4Hi9FN202 (M+H) 267.3, found 267.0.

The synthetic route of 630-17-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DUDKIN, Vadim; FRALEY, Mark, E.; ARRINGTON, Kenneth, L.; LAYTON, Mark, E.; RODZINAK, Kevin, J.; PERO, Joseph, E.; REIF, Alexander, J.; WO2012/21382; (2012); A1;,
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Some common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, molecular formula is C3H5Br, 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. Recommanded Product: 4333-56-6

guanidine hydrochloride 100 kg with the bromo cyclopropane 126.6 kg placed in 800 kg in acetone, then adding the potassium carbonate 174.6 kg, heating to 50 C, reaction 3.5h, dropped to room temperature after-filtration, the filtrate is concentrated under reduced pressure to dry, to produce an intermediate 198.6 kg, molar yield 95%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4333-56-6, its application will become more common.

Reference:
Patent; QILU SYNVA PHARMACEUTICAL CO., LTD.; LIU, ZHI; KONG, QINGWEN; FANG, MINGFENG; LIU, QUANCAI; KONG, MEI; WU, LIANYONG; (6 pag.)CN104649982; (2016); B;,
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Application of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask containing aqueous sulfuric acid (14%, 260 mL), 3-bromo-2-methylaniline (5.00 mL, 40.6 mmol) was added. The mixture was brought to reflux, and a solution of sodium nitrite (3.08 g, 44.6 mmol) in water (minimum amount required to dissolve) was added dropwise over the course of 1 hour. The mixture was refluxed an additional 30 minutes, cooled to room temperature, and extracted three times with chloroform. The combined chloroform layeres were extracted three times with aqueous sodium hydroxide (1 M). The aqueous layers were acidified with concentrated hydrochloric acid and extracted three times with chloroform. These three chloroform extracts were combined, dried over magnesium sulfate, filtered, and concentrated to give 3-bromo-2-methylphenol (10-1, 5.63 g) as a brown solid.

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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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 1003-99-2, Safety of 2-Bromo-5-fluoroaniline

To a solution of 2-bromo-5-fluoroaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at 0° C. under N2 atmosphere was added dropwise 1M NaHMDS (2.5 eq.). The reaction was stirred for 15 minutes at 0° C., and a solution of di-tert-butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5percent ethyl acetate in hexane to give the product as light yellow oil.

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

Reference:
Patent; GlaxoSmithKline Biologicals SA; Skibinski, David; Jain, Siddhartha; Singh, Manmohan; O’Hagan, Derek; (124 pag.)US9408907; (2016); B2;,
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2695-47-8, name is 6-Bromo-1-hexene, 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. HPLC of Formula: C6H11Br

To a suspension of tosylamide (50.25 g, 293.5 mmol) and K2CO3 (17.28 g, 125.0 mmol) inDMSO (250 ml) was added 6-bromo-1-hexene (S3, 13.36 ml, 100.0 mmol) at room temperature.After stirring for 15 h at room temperature, the reaction mixture was filtered through a shortplug of Celite and partitioned between diethyl ether and H2O. The aqueous phases wereextracted twice with diethyl ether. The combined organic phases were washed with brine, driedover MgSO4, filtered and concentrated under reduced pressure. The residue was purified byflash column chromatography (20% EtOAc/hexane) to afford S4 (20.05 g, 78.15 mmol, 78%) asa yellow oil.

The synthetic route of 2695-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Orihara, Kensuke; Kawagishi, Fumiki; Yokoshima, Satoshi; Fukuyama, Tohru; Synlett; vol. 29; 6; (2018); p. 769 – 772;,
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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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-4-fluoroaniline

A solution of sodium nitrite (4.2 g , 60 mmol) was added drop-wise to a mixture of 3-bromo-4-fluoroaniline (11.2 g, 58.9 mmol) and concentrated HCl (30 mL, 0.36 M) at 0 0C over 30 min. The resulting clear solution was stirred for 45 min, and a solution of SnCl2*2H2O (27 g, 120 mmol) in concentrated HCl (30 mL) was added drop-wise at 0 0C over 1.5 h. The mixture was stirred for 18 h at room temperature. The resulting precipitate was collected by filtration and crystallized from ethanol to provide the title compound (6.2 g, 42 %) as a yellow powder: 1H NMR (300 MHz, DMSO-J6) delta 10.24 (s, 3H), 8.42 (s, IH), 7.36-7.30 (m, 2H), 7.03-6.98 (m, IH).

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
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Synthetic Route of 2550-36-9, These common heterocyclic compound, 2550-36-9, name is (Bromomethyl)cyclohexane, 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.

Step 1 : To a solution of 3-bromo-6-methylimidazo[1,5-a]pyrazin-8(7H)-one (1 g, 4.39 mmol, 1 eq) and Cs2CO3 (2.86 g, 8.78 mmol, 2 eq) in DMF (20 mL) was added (bromomethyl)cyclohexane (1.55 g, 8.78 mmol, 1.22 mL, 2 eq). The mixture was stirred at 60C for 18 hour. The reaction mixture was filtered and the filtrate was concentrated. The crude mixture was purified by flash chromatography with petroleum ethenethyl acetate = 5:1 ~ 3: 1. 3-bromo-7-(cyclohexylmethyl)-6-methylimidazo[1,5-a]pyrazin-8(7H)-one (1 g, 3.02 mmol, 69% yield) was obtained. 1H NMR (CDCl3 , 400 MHz): delta 7.86 (s, 1 H), 6.80 (s, 1 H), 3.79 (6, J = 1.2 Hz, 2H), 2.29 (s, 3H), 1.75 -1.66 (m, 6H), 1.22 – 1.04 (m, 5H). LC-MS: tR = 0.791 min (method 15), m/z = 325.9 [M + H]+.

The synthetic route of 2550-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
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Related Products of 460-00-4, 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. 460-00-4, name is 1-Bromo-4-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200-300 mesh) column.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Lei; Ji, Enhui; Liu, Ning; Dai, Bin; Synthesis; vol. 48; 5; (2016); p. 737 – 750;,
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Electric Literature of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-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.

2-Bromo-l,4-difluorobenzene(53.6 g, 277.74 mmol) in THF cooled to -50C was added to isopropyl magnesium chloride (2M in THF)( 133mL, 266 mmol). The reaction mixture thus obtained was warmed to 0C and stirred for lh. The reaction mixture was cooled again to -50C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200mL) was added dropwise to this reaction mixture with stirring and the stirring was continued at 0C for lh. The reaction mixture was quenched with saturated aqueous NH4C1 solution, extracted with ethylacetate. The organic layer collected was washed with water (500 mL) and then with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude liquid residue. The residue thus obtained was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent) to afford 35 g of the title compound as a colourless liquid. 1H NMR (300MHz, CDC13) delta ppm 7.6-7.53(lH, m), 7.26-7.09(2H, m), 3.7(2H, t) 3.22- 3.14(2H, m), 2.28-2.16(2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; SASMAL, Pradip Kumar; AHMED, Shahadat; TEHIM, Ashok; PRADKAR, Vidyadhar; DATTATREYA, Prasanna M.; MAVINAHALLI, Nanjegowda Jagadeesh; WO2013/88256; (2013); A1;,
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