Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-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 656-64-4, Application In Synthesis of 3-Bromo-4-fluoroaniline

General procedure: A stirred mixture of compound 5 (0.23 g, 0.001 mol), EDCI (0.23 g, 0.0012 mol), HOBt (0.16 g,0.0012 mol), aniline or aniline derivative (0.001 mol), and 20 mL DMF was reacted at room temperature overnight, and then 40 mL water was added and stirred for a quarter, before the crude was filtered and washed twice with water. The anticipated product was purified by column chromatography on silicagel using petroleum ether/ethyl acetate (2/1, volume ratio) as the eluent to afford the target compound.

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Reference:
Article; Deng, Xinshan; Tan, Xiaoyu; An, Tiantian; Ma, Qingqing; Jin, Zhe; Wang, Ce; Meng, Qingguo; Hu, Chun; Molecules; vol. 24; 4; (2019);,
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Synthetic Route of 202865-83-6, These common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, 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: Preparation of 8-(3-fluoro-5-methyl-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane A mixture of 1,4-dioxa-8-azaspiro[4.5]decane hydrochloride (4.0 g, 22.3 mmol), 1-bromo- 3-fluoro-5-methylbenzene (5.05 g, 26.7 mmol), Pd2(dba)3 (408 mg, 445 mumol), Ruphos (416 mg, 891 mumol) and Cs2CO3 (18.1 g, 55.7 mmol) in toluene (50 mL) was heated with stirring at 120 C for 15 hrs. The resulting reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to give 8-(3-fluoro-5- methyl-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (5.0g) as a yellow oil.

Statistics shows that 1-Bromo-3-fluoro-5-methylbenzene is playing an increasingly important role. we look forward to future research findings about 202865-83-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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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 452-63-1 as follows. Recommanded Product: 452-63-1

A screw-capped vial (8 mL) was charged with compound 538 (100 mg, 0.37 MMOL) in 1,4-dioxane (2 mL), 2-bromo-5-fluoro-toluene (55 LULL, 0.44 MMOL), CS2C03 (169 mg, 0.52 MMOL), PD2 (dba) 3 (9 mg, 0.009 MMOL), and rac-BINAP (9 mg, 0.014 MMOL). The tube was capped with a rubber septum, flushed with argon for 5 min, and then stirred at 100 C for 18 h. The reaction mixture was allowed to cool to room temperature, and then poured into a mixture of water and EtOAc. The aqueous phase was extracted twice with more EtOAc. The combined organic phases were washed with brine, dried (MgS04), filtered and concentrated in vacuo. The crude product was purified by chromatography eluting with EtOAc/petroleum ether 1: 3 to afford the title compound as light brown oil.

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; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Bromide – Wikipedia,
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Electric Literature of 134168-97-1,Some common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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.

A solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (380 mg, 2.0 mmol) and 1-(2-chloroethyl)pyrrolidine (CAS 505041-9) (380 mg, 2.2 mmol) in NMP (20 mL) was heated to 120 C. overnight. The solution was diluted with EtOAc (100 mL) and washed with saturated Na2CO3 aqueous solution (3*40 mL). The combined organic layer were dried over Na2SO4, concentrated and purified by prep-TLC (DCM: MeOH=10:1) to give the titled product (290 mg, 50%). LCMS (0-60 AB), RT=1.076 min, M+H, 289.0

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

Reference:
Patent; Chen, Huifen; Crawford, Terry; Harris, Seth F.; Magnuson, Steven R.; Ndubaku, Chudi; Wang, Lan; US2013/324516; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H11Br

A solution of diethyl malonate (36.91 g, 230.4 mmol), anhydrous methanol (400 mL), and NaOMe (25% in methanol, 49.79 g, 230.4 mmol) is stirred at reflux for one hour under nitrogen. Bromomethyl-cyclopentane (31.31 g, 192.0 mmol) is added to the mixture, and stirred for an additional 3 hours. A solution of NaOH (23.04 g, 576.0 mmol) in water (400 mL) is added, and the mixture is stirred for an additional 1 hour at reflux. The mixture is cooled, diluted with water, and extracted with ether. The ether layer is discarded, and the aqueous layer is acidified with 1N HCl to pH=1. The aqueous layer is extracted with EtOAc. The EtOAc layers are combined, dried over Na2SO4, and concentrated. This gives 2-cyclopentylmethyl-malonic acid (21.0 g, 59% yield) as a white solid.

According to the analysis of related databases, 3814-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lee, Kwangho; Leeds, Jennifer A.; US2009/62537; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2550-36-9, 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. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2,6-Dihydroxyacetophenone 7 (1.0equiv.) was dissolved in acetone (10mL) and then anhydrous potassium carbonate (2.0equiv.) with corresponding alkyl bromides (1.0equiv.) were added and the reaction mixture was stirred at 80C for overnight. After evaporating the solvent under reduced pressure the reaction mixture was further diluted with dichloromethane (20mL) and washed with water (20mL×3). The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by flash column chromatography to afford the title compounds 8. 6.1.1.1 1-(2-(Cyclohexylmethoxy)-6-hydroxyphenyl)ethanone (8a) Yield 50%; Yellow colored solid; 1H NMR (CDCl3) delta 13.20 (s, 1H), 7.29 (t, J = 8.4 Hz, 1H), 6.53 (d, J = 8.4 Hz, 1H), 6.40 (d, J = 8.4 Hz, 1H), 3.81 (d, J = 6.0, 2H), 2.72 (s, 3H), 1.69-1.87 (m, 5H), 1.19-1.29 (m, 6H).

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Hyun-Sun; Venkateswararao, Eeda; Boggu, Pulla Reddy; Sharma, Vinay K.; Kim, Youngsoo; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4330 – 4338;,
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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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Bromophenylacetylene

Step B: 4-[(3-Bromophenyl)ethynyl]-2-chloro-5-fluoropyrimidine; To an oven-dried flask under N2 was added 2,4-dichloro-5-fluoropyrimidine (1.66 g, 10 mmol), anhydrous, degassed THF (100 mL), dichlorobis(triphenyl-phosphine)palladium(II) (180 mg, 0.26 mmol), copper(I) iodide (29 mg, 0.15 mmol), and TEA (2.02 g, 20 mmol). After heating the reaction at 60 C. for 30 min, 1-bromo-3-ethynylbenzene (0.9 g, 5.0 mmol) was added dropwise as a solution in THF (25 mL) and the resulting mixture was allowed to heat overnight. The crude reaction mixture was adsorbed to silica gel and purified by column chromatography (2-10% EtOAc in hexanes) to afford the desired product (1.25 g, 78%) as an off white solid. ESIMS (M+H)+=311.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US2008/51395; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1798-85-2,Some common heterocyclic compound, 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene, molecular formula is C9H9Br, 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.

A stirred suspension oflntermediate B-4 (201.8 mg, 0.647 mmol), 1-bromo-3-cyclopropylbenzene (246.7 mg, 1.252 mmol), Pd2(dba)3 (58.5 mg, 0.064 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (“X-Phos”) (30.7 mg, 0.064 mmol)and potassium carbonate (414.7 mg, 3.00 mmol) in t-BuOH (4.0 mL) was degassed(pump/N2 x 3) and then heated to 80 oc overnight. The reaction mixture was cooled to20 room temperature. The mixture was diluted with EtOAc, filtered through a 4 )lmmembrane filter, concentrated, and then dried under vacuum. The residue was purifiedby flash chromatography (Teledyne ISCO CombiFlash Rf, gradient ofO% to 100% using solvent A/B=heptane/EtOAc over 15 column volumes, REDISEP Si02 40g, loaded asDCM solution). Obtained Intermediate B-12A (134.0 mg, 48%) as a tan solid: HPLC_RT=2.218 min (Waters SunFire C18 2.1x30mm, MeOH/H20/0.1% TFA, 2min gradient,wavelength= 254 nm); MS(ES): m/z= 372/374 [M-t-Bu+ It; 1H NMR (400 MHz,5 chloroform-d) 8 7.05-7.15 (m, IH), 6.59 (d, J=7.70 Hz, IH), 6.47-6.55 (m, 2H), 5.61 (d,J=7.26 Hz, IH), 4.53-4.65 (m, IH), 4.26-4.33 (m, IH), 3.66 (dd, J=9.57, 11.77 Hz, IH),1.75-1.85 (m, IH), 1.46 (s, 9H), 0.85-0.97 (m, 2H), 0.57-0.71 (m, 2H).

The synthetic route of 1798-85-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILL, Patrice; QUESNELLE, Claude A.; SAULNIER, Mark G.; GAVAI, Ashvinikumar V.; WO2014/47369; (2014); A1;,
Bromide – Wikipedia,
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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. Formula: C6H3BrF2

-Bromo-1,4-difluorobenzene (53.6 g, 277.74 mmol) in THF (50 ml) was cooled to -50 C., to it was added isopropyl magnesium chloride (2M in THF) (133 mL, 266 mmol). The reaction mixture thus obtained was warmed to 0 C. and stirred for 1 h. The reaction mixture was cooled again to -50 C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200 mL) was added drop wise to this reaction mixture with stirring and the stifling was continued at 0 C. for 1 h. The reaction mixture was quenched with saturated aqueous NH4Cl 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 colorless liquid. 1H NMR (300 MHz, CDCl3) delta 7.60-7.53 (1H, m), 7.26-7.09 (2H, m), 3.70 (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 399-94-0, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; Sasmal, Pradip Kumar; Ahmed, Shahadat; Tehim, Ashok; Paradkar, Vidyadhar; US2015/368238; (2015); A1;,
Bromide – Wikipedia,
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Reference of 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.

The compounds of the formula (I-7-1) A reaction vessel 10.0 g (0.052 mol), 1- pentyne 4.6 g(0.067 mol), copper iodide (I) 0.20g (1 .0 mmol), was added N, N-dimethylformamide 120 mL,triethylamine 40 mL. After the inside of the system was replaced with nitrogen, tetrakis(triphenylphosphine) palladium (0) 0.60 g (0.52 mmol) was added and heating for 12 hoursstirring at 90 ° C. After dilution with toluene, hydrochloric acid, washed with brine, and purifiedby column chromatography (silica gel) to give the formula (the I-7-2) with the compoundrepresented by 7.0 g (0.039 mol) .

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-2,3-difluorobenzene, its application will become more common.

Reference:
Patent; DIC CORPORATION; HORIGUCHI, MASAHIRO; HAYASHI, MASANAO; KUSUMOTO, TETSUO; (71 pag.)JP2015/78153; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary