Tag: M.W=200-300

Synthetic Route of 1193389-40-0, The chemical industry reduces the impact on the environment during synthesis 1193389-40-0, name is 1-(4-Bromophenyl)cyclobutanamine hydrochloride, I believe this compound will play a more active role in future production and life.

The free base of commercially available [1 -(4-bromo-phenyl)-cyclobutyl]-amine hydrochloride [CAS 1 193389-40-0] (8.99 g, 34.24 mmol) was prepared as follows: (8.99 g, 34.24 mmol) of the hydrochloride salt was taken up in DCM and washed sequentially with aqueous sodium bicarbonate and water and the organic portion was tried and concentrated.The crude amine was taken up in dry THF (120 mL) and diisopropylethylamine (17.62 mL, 102.71 mmol) under nitrogen and a solution of di-tert-butyldicarbonate (8.22 g, 37.66 mmol) in THF (20 mL) was added. The reaction was stirred at rt overnight. The mixture was partitioned between EtOAc and water and the extracted organic phase was washed with brine and concentrated in vacuo to give the title compound.

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-(4-Bromophenyl)cyclobutanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; INCE, Stuart; HAEGEBARTH, Andrea; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; SCOTT, William; WO2012/7345; (2012); A2;,
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Synthetic Route of 67344-77-8, A common heterocyclic compound, 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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.

To a solution of 1-(3-bromophenyl)-N-methylmethanamine (6; 45.6 g, 228 mmol) in CH2Cl2 (700 mL) were added N-(tert-butoxycarbonyl)glycine (43.9 g, 251 mmol), WSCD*HCl (52.4 g, 274 mmol), and HOBt (37.1 g, 275 mmol). After being stirred at room temperature for 1 week, the mixture was diluted with water and the mixture was extracted with CHCl3. The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/EtOAc = 7:1 to1:1) to give the product (49.1 g, 60percent) as an oil. 1H NMR (CDCl3): this compound exists as a pair of rotamers at room temperature. d 1.44 (minor rotamer, 9H, s), 1.46 (major rotamer, 9H, s), 2.90 (major rotamer, 3H, s), 2.98 (minor rotamer, 3H, s), 3.96?4.06 (2H, m), 4.44 (minor rotamer, 2H, s), 4.57 (major rotamer, 2H, s),5.54 (1H, br s), 7.06?7.25 (2H, m), 7.28?7.49 (2H, m); MS (ESI) m/z [M+H]+ 357, 359.

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; Yamaki, Susumu; Suzuki, Daisuke; Fujiyasu, Jiro; Neya, Masahiro; Nagashima, Akira; Kondo, Mitsuhiro; Akabane, Takafumi; Kadono, Keitaro; Moritomo, Ayako; Yoshihara, Kosei; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 187 – 201;,
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69321-60-4, name is 2,6-Dibromotoluene, 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. Quality Control of 2,6-Dibromotoluene

24.1) 1-Benzylsulfanyl-3-bromo-2-methyl-benzene (Intermediate 83): 2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 1000C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography. Yield: 17g, 72 %

The synthetic route of 69321-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2009/103440; (2009); A1;,
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Related Products of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCl2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and NaOH 1N (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compoundwas obtained as a cream powder (2.5g, 54.74%); m.p. 126-128C

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; SMITHKLINE BEECHAM CORPORATION; WO2004/111046; (2004); A2;,
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Electric Literature of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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 1 L round bottom flask equipped with a reflux condenser under argon, a mixture of 1,4-dibromo-2,5-difluorobenzene (53.7 g, 197 mmol), (2-methoxyphenyl)boronic acid (20 g, 132 mmol), potassium phosphate monohydrate (60.5 g, 263 mmol) in dimethoxyethane (DME) (590 mL) and water (65 ml) was bubbled with argon for 10 min, then tetrakis (1.521 g, 1.316 mmol) was added and the reaction mixture was refluxed at 82 C. for 8 hours. The reaction was monitored by liquid chromatography-mass spectroscopy (LCMS). The reaction mixture was cooled to room temperature and treated with water (200 ml). The aqueous layer was separated and extracted several times with ethyl acetate (300 ml each). The organic layer was washed with brine (200 mL), dried with Na2SO4, filtered, concentrated, and dried in vacuo. The crude product was chromatographed on a 220 g gold SiO2 column eluting with 0-40% EtOAc/Hexane to yield 5-bromo-2,4difluoro-2?-methoxy-1,1?byphenyl as clear oil (19.68 g, 50% yield).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; JI, Zhiqiang; TSAI, Jui-Yi; DYATKIN, Alexey Borisovich; LIN, Chun; US2019/233451; (2019); A1;,
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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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2,4,5-trifluorobenzene

A 1-L, one-necked, round-bottom flask, equipped with a Tefloncoatedmagnetic stirring bar, was removed from a drying oven at150 C, sealed while hot with a rubber septum, purged with dry N2,and cooled to r.t. (22 C). 1-Bromo-2,4,5-trifluorobenzene (1; 50.0mL, 90.0 g, 0.427 mol; Oakwood Products) and anhydrous THF(400 mL) were added from a syringe, and the flask was submergedin a bath of acetone cooled to -78 C with dry ice. A 2.0 M solutionof DIPEA in THF (224 mL, 0.448 mol; Sigma-Aldrich) was addedwith stirring over 5 min, and the resulting mixture was stirred for anadditional 10 min. The dry ice-acetone bath was removed and replacedwith an ice-water bath. The mixture was stirred for an additional30 min then the ice-water bath was removed and the flaskwas resubmerged in the dry ice-acetone bath. The mixture wasstirred for 10 min at -78 C, then aldehyde 2 (50.4 mL, 71.7 g, 0.448mol; Oakwood Products) was added from a syringe. The resultingmixture was stirred for an additional 10 min before the dry ice-acetone bath was removed. The flask was then warmed to r.t., andthe mixture was stirred at r.t. for 3 h. The reaction was thenquenched by addition of sat. aq NH4Cl (50 mL), and the resultingbiphasic mixture was diluted with H2O (300 mL) and Et2O (200mL). The two phases were separated, and the aqueous fraction wasextracted with Et2O (2 × 300 mL). The organic fractions were combined,dried (Na2SO4), and concentrated by rotary evaporation togive alcohol 3 as a viscous oil.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Woydziak, Zachary R.; Fu, Liqiang; Peterson, Blake R.; Synthesis; vol. 46; 2; (2014); p. 158 – 164;,
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Related Products of 24358-62-1,Some common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, molecular formula is C8H10BrN, 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.

EXAMPLE 193A 1-bromo-4-(1-isocyanatoethyl)benzene The title compound was prepared using the procedure described in Example 61A using 1-(4-bromophenyl)ethylamine instead of 5-aminoisoquinoline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Bromophenyl)ethylamine, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6933311; (2005); B2;,
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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. 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 176317-02-5

EXAMPLE 4 This Example illustrates the preparation of 1,1-bis(4-trifluoromethoxyphenyl)-2-(2H-tetrazol-2-yl)propanol (compound no. IX, Table I). A proportion (ca. 25 cm3) of a solution of 4-bromotrifluoromethoxybenzene (45.79 g) in dry tetrahydrofuran (200 cm3) was added to a gently stirred mixture of magnesium turnings (4.56 g) and dry tetrahydrofuran and a crystal of iodine under a nitrogen atmosphere. When the exothermic reaction had commenced the temperature of the mixture was maintained at the reflux temperature by the careful addition of the remaining 4-bromotrifluorobenzene followed by heating the mixture for a further hour at the reflux temperature. The mixture was cooled to the ambient temperature and stirred under a nitrogen atmosphere whilst a solution of methyl 2-(2H-tetrazol-2-yl)propionate (13.95 g) in dry tetrahydrofuran (60 cm3) was added dropwise, followed by heating the mixture at the reflux temperature for 30 minutes. The mixture was cooled and poured into water (500 cm3) and the resultant mixture acidified with 2N hydrochloric acid (250 cm3) and extracted with diethylether (3*400 cm3). The extracts were combined, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvents under reduced pressure to give a residual oil (30.5 g). This was subjected to purification by chromatography on a silica gel column using a mixture of n-hexane (4 parts by volume) and ethyl acetate (1 part by volume), and thereafter by h.p.l.c. of the fractions containing the product using the same eluant, to yield 1,1-bis(4-trifluoromethoxyphenyl)-2-(2H-tetrazol-2-yl)propanol (10.0 g), which crystallized on standing to a white solid, m.p. 68-70 C. Nmr (CDCl3) delta: 1.55 (d, 3H); 4.8 (s, 1H); 6.1 (q, 1H); 7.4 (m, 8H); 8.4 (s, 1H).

According to the analysis of related databases, 176317-02-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Imperial Chemical Industries PLC; US4831047; (1989); A;,
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These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. Recommanded Product: 22385-77-9

A solution of diisopropylamine (8.33 mL,59.5mmol) in THF (20 mL) was treated with n-BuLi (36.1 mL,1.65M in hexane, 59.5 mmol), and the resulting solution of lithium diisopropylamide (LDA) was added to a solution of ferrocenyl phenyl sulfoxide (6) (12.3 g, 39.7mmol) in THF (100 mL) at -78 °C. After stirring at -78 °C for 30 min, the resulting solution was transferred to a suspension of ZnCl2 (16.2 g, 119 mmol) in THF (100 mL) at -78 °C. After stirring at -78 °C for 1 h, the reaction mixture was warmed to room temperature, where stirring was maintained for 1 h. The resulting solution was added to a solution of 1-bromo-3,5-di-t-butylbenzene (10.7 g, 39.7mmol) and [Pd(PPh3)4] (2.30 g, 1.99 mmol) in THF (50 mL). The reaction mixture was heated at 60 °C for 10 h, and then the reaction was quenched with a saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with Et2O, and the combined organic phases were washed with water and dried over MgSO4. After filtration, the filtrate was evaporated to remove the solvent under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethylacetate 1:1) to give 7 (16.8 g, 33.7mmol, 85percent).

The synthetic route of 1-Bromo-3,5-di-tert-butylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakagami, Michiyasu; Sasamori, Takahiro; Sakai, Heisuke; Furukawa, Yukio; Tokitoh, Norihiro; Bulletin of the Chemical Society of Japan; vol. 86; 10; (2013); p. 1132 – 1143;,
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Related Products of 1435-51-4, A common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

To mixture of l,3-dibromo-5-fluorobenzene (LXXXV) (100 g, 393 mmol) and N’,N’-dimethylethane-l,2-diamine (173 g, 1.97 mol, 214 mL) was added t-BuOK (88 g, 787 mmol) in one portion at 25C under N2. The mixture was stirred at 25C for 30 min, then heated to 110C and stirred for 11.5 h. The mixture was cooled to 25C and concentrated in reduced pressure at 45C. The residue was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100-200 mesh silica gel, PE/EtOAc = 2: 1, Rf = 0.6) to give N:-(3- bromo-5-fluorophenyl)-N2,N2-dimethylethane-l,2-diamine (LXXXVI) (30 g, 114.9 mmol, 29.2% yield) as a yellow oil. ESIMS found for Ci0Hi4BrFN2 mlz 261.1 (M+H).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
Bromide – Wikipedia,
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