Tag: M.W=200-300

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 588-96-5 as follows. Recommanded Product: p-Bromophenetole

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo phenetole (3.19 ML, 22.2 mmol, 1.2 eq. ) and NEt3 (6.22 ML, 44.6 mmol, 2.4 eq. ) in CH3CN (40 ml), was added a sonicated (for 2 min) suspension of P (O-TOL) 3 (0.57 g, 2.22 mmol, 0.1 eq. ) and Pd (OAC) 2 (209 mg, 5%) in CH3CN (5 ML). The reaction mixture was heated to reflux for 2 hrs. CH3CN was removed under vacuo. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 ML) and with brine (50 ML). A purification by flash chromatography afforded the desired 2R- [3- (4-ETHOXY-PHENYL)-ALLYL]-3S- hydroxy-succinic acid diisopropyl ester (5.92 g, 84% yield).

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERNALIS (OXFORD) LIMITED; LABORATOIRES SERONO S.A.; WO2005/19194; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, belongs to ethers-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 18800-30-1, Computed Properties of C8H8Br2O

EXAMPLE 1 A mixture of 2.8 parts of 1-bromo-4-(2-bromoethoxy)benzene, 5 parts of cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3-H1,2,4-triazol-3-one, 0.7 parts of potassium hydroxide and 100 parts of dimethyl sulfoxide was stirred for 4 hours at room temperature. The reaction mixture was poured into water. The product was extracted with dichloromethane. The extract was subsequently washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel usinq a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2′-oxybispropane. The product was filtered off and recrystallized from methylbenzene, yielding 5.2 parts (79%) of cis-2-[2-(4-bromophenoxy)ethyl]-4-[4-[ 4-[4-[[2-(2,4-dichlorophenyl)-2-(1 H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one; mp. 143.3 C. (compound 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(2-bromoethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica, N.V.; US4791111; (1988); 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. 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 452-08-4

106 ml of 2.5 M butyllithium in hexane are added dropwise at -20 C. to a solution of 2-bromo-4-fluoro-1-methoxy-benzene (50 g) in 1 l of pentane, and stirred for 15 min at -10 C., then cooled to -30 C. Then trimethylborate (30 ml) is added, stirred 30 min at 0 C., cooled to -10 C., followed by the addition of a 32% peracetic solution (103 ml) over 45 min keeping the temperature to below -5 C. and stirring 30 min at 0 C. The mixture is cooled to -10 C., 150 ml of a saturated NaHSO3 solution are added, stirred 1 h at AT, then after adding water, neutralizing with 330 g of NaHCO3 and decanting the pentane, the aqueous layer is extracted with DCM. The organic layer is washed with sodium hydroxide, the aqueous layer is acidified with a concentrated HCl solution, extracted with DCM and the organic layer is dried over MgSO4, filtered and concentrated to dryness. 27.1 g of desired product are obtained.

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; CEREP; US2009/233910; (2009); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13BrO

Compound 38E: Methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)- 1 /-/-pyrrole-2-carboxylate.A mixture of methyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2- carboxylate (Compound 38F, 600 mg, 2.39 mmol) and 1-bromo-3-benzyloxypropane (575 mg, 2.51 mmol) in DMF (2.19 mL) was charged with cesium carbonate (778 mg, 2.39 mmol). The reaction mixture was allowed to stir at 70 °C for 16 hrs. The reaction mixture was diluted with water and then extracted with EtOAc (2x). The organic layer was washed with water (2x), brine (1 x), dried over Na2S04, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash.(R). Rf system [0–> 4percent Ethanol in DCM] to afford 442mg of the title compound (46percent). 1H NMR (400 MHz, CD3OD) delta 7.26 – 7.37 (m, 5H), 7.25 (d, J = 1 .8 Hz, 1 H), 7.17 (d, J = 1.8 Hz, 1 H), 4.45 (s, 2H), 4.42 (t, J = 6.8 Hz, 2H), 3.78 (s, 3H), 3.38 (t, J = 5.9 Hz, 2H), 2.01 (t, J = 6.2 Hz, 2H), 1 .31 (s, 12H). MS (ESI): m/z 440.59 [M+H]+. UPLC: tR = 1.60 min (UPLC-TOF: polar_2 min).

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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); A1;,
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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. 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C15H23BrO

In a 300 mL reactor sufficiently dried and purged with argon, 0.46 g (18.8 mmol) of magnesium pieces were charged and vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a piece of iodine and 20 mL of tetrahydrofuran were charged and stirred. To this solution, J.Am. Chem. Soc. 2006, 128, 16486. A 30 mL dilute solution of 5.17 g (17.3 mmol) of 1-bromo-3,5-di-tert-butyl-4-methoxybenzene synthesized by the method described above was added dropwise (1.0 mL added)After that, the mixture was heated to reflux until the color of iodine disappeared with a drier, and after the start of the reaction, the remaining droplets were dropped), and after completion of the dropwise addition, the mixture was heated to reflux in an oil bath at 80 C. for 1 hour.The reaction solution was cooled to -78 C., 2.20 mL (19.8 mmol) of trimethoxyborane was slowly added, and stirring was continued for 19 hours while slowly returning to room temperature. An aqueous solution of 1.0 M hydrochloric acid was added, the solubles were extracted with di-iso-propyl ether, and the obtained fraction was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated to give a residue, which contains 3.38 g (15.0 mmol) of the compound (A-4a) obtained in Synthesis Example 4-1, tripotassium phosphate 7. 34 g (34.6 mmol), 0.03 g (0.15 mmol) of palladium acetate, 2-dicyclohexylphosphino-2 ‘, 6’-dimethoxybiphenyl (0.10 g (0.23 mmol) of S-Phos), 35 mL of tetrahydrofuran and 7 mL of distilled water were charged, and the mixture was heated under reflux for 2 hours in an oil bath. The reaction solution is cooled to room temperature, a saturated aqueous ammonium chloride solution is added, and the soluble matter is extracted with n-hexane and ethyl acetate to obtainThe fraction was washed with brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the desired product represented by the following formula (A-4b) (hereinafter referred to as compound (A-4b)) Is 5.44 g (yield 99%) were obtained.

According to the analysis of related databases, 1516-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
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Synthetic Route of 175278-09-8, 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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

1b. Preparation of 1 -bromo-3-trifluoromethoxybenzene. 2579.53 g of 2-propanol and 1100 g of the product from stage Ia are placed in a 10 litre lined glass reactor with 4 necks and outlet on bottom, and a previously prepared solution of 382.52 g of NaNO2 in 766.18 g of water is added. 459.6 g of concentrated sulphuric acid are then metered slowly. The acids are diluted and the upper organic phase is separated from the lower aqueous phase. The organic phase is washed and a first organic phase and an upper aqueous phase are separated. The latter is further diluted with water until a second organic phase is released. This organic phase is added to the first and everything is washed again, separating an aqueous phase and an organic phase which, after being anhydrified with CaCl2, undergoes distillation to provide the product indicated in the title (final yield 84%). B.p. 156-158C/760 mmHg.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-(trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MITENI S.P.A.; WO2007/107820; (2007); A2;,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, A new synthetic method of this compound is introduced below., name: 1-(Benzyloxy)-3-bromobenzene

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.2 g, 0.76 mmol), 3- cyanophenylboronic acid (0.223 g, 1.52 mmol), barium hydroxide (0.285 g, 1.67 mmol), Pd(PPh3)4 (0.088 g, 0.076 mmol), DME (5 mL) and H2O (3 mL) was heated (800C) for 6 hours with vigorous stirring under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of celite. The filtrate was diluted with brine; the organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue obtained was purified by flash column chromatography (20% diethyl? ether-hexane) to give 75 (0.130 g, 60% yield) as a viscous liquid. 1H NMR (500 MHz, CDCl3) delta 7.85 (t, J = 2.5 Hz, IH), 7.78 (dt, J = 7.5 Hz, J = 1.5 Hz, IH), 7.63 (dt, J = 8.0 Hz, J = 1.5 Hz, IH), 7.53 (t, J = 8.0 Hz, IH), 7.46 (d, J = 7.5 Hz, 2H)5 7.44- 7.37 (m, 3H)5 7.35 (t, J = 7.0 Hz, IH), 7.18-7.14 (m, 2H), 7.02 (dd, J = 8.5 Hz5 J = 2.5 Hz, IH)5 5.17 (s, 2H).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF CONNECTICUT; WO2008/13963; (2008); A2;,
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Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

General procedure: To a 30 mL flamed-dried flask equipped with stir bar and a nitrogen-filled balloon were added 2,2,6,6-tetramethylpiperidine (1.2 equiv) and THF (12 mL). After cooled to 0 C with an ice waterbath, n-BuLi (2.5 M in hexane, 1.2 equiv) was added dropwise and the reaction was stirred at 0 C for 0.5 h. To a 100 mL flame-dried flask equipped with a stir bar and a nitrogen-filled balloon were added THF (30 mL), benzyne precursor (1 equiv), and corresponding ketene silyl acetals9 (1.5 equiv) and was cooled to 78 C with an acetone-dry ice bath before in situ generated lithium tetramethylpiperidine was added dropwise. The reaction was monitored and aqueous NH4Cl was added upon disappearance of the benzyne precursor. After warming to rt, the reaction mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and concentrated under reduced pressure. Acetonitrile (30 mL) was added to the concentrated reaction system and cooled to 0 C with an ice-water bath followed by slow addition of hydrofluoric acid (27.6 M, 10 equiv). Upon completion, the reaction was heated to 40 C overnight before water (100 mL) was added. The mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and dried with Na2SO4. The combined organic extract was concentrated under reduced pressure and purified by column chromatography on silica gel to afford the following compounds. 4.6.1. 5-(Benzyloxy)-8-methylbicyclo[4.2.0]octa-1,3,5-trien-7-one (9). Compound 9 was obtained as light yellow oil (271 mg) from 6d and tert-butyl((1-methoxyprop-1-en-1-yl)oxy)dimethylsilane in 23% yield, Rf=0.6 (Hexane/EtOAc=5:1); 1H NMR (400 MHz, CDCl3) delta 7.48-7.30 (m, 6H), 7.02 (d, J7.0 Hz, 1H), 6.89 (d, J8.4 Hz, 1H), 5.45 (s, 2H), 4.21 (q, J7.2 Hz, 1H), 1.47 (d, J7.2 Hz, 3H). 13C NMR (101 MHz, CDCl3) delta 189.3 (s), 157.0 (s), 152.6 (s), 137.8 (s), 136.4 (s), 130.7 (s), 128.5 (s), 128.2 (s), 127.9 (s), 116.7 (s), 114.2 (s), 74.0 (s), 58.3 (s), 15.0 (s). IR: gamma 2964, 2927, 2360, 2342, 1756, 1602, 1571, 1473, 1452, 1386, 1273, 1161, 1125, 991, 886, 795, 767, 748, 699 cm-1. HRMS calcd for C16H14NaO2 [M+Na]+: 261.0886, found: 261.0879.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen; Savage, Nikolas A.; Dong, Guangbin; Tetrahedron; vol. 70; 27-28; (2014); p. 4135 – 4146;,
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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. 22171-15-9, name is (4-(Benzyloxy)phenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 22171-15-9

2-Amino-6-chloro-nicotinic acid described in Preparation Example A-1 (220mg, 1.4mmol), triethylamine (0.47mL, 3.37mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (764mg, 1.73mmol) were dissolved in N,N-dimethylformamide (3mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (399mg, 1.87mmol) was added thereto, followed by stirring at room temperature for 17 hours 30 minutes. After the reaction was completed, the reaction solution was poured into brine, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 1), and the title compound (115mg, 0.31 mmol, 22%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm): 4.35 (2H, d, J=6.0Hz), 5.08 (2H, s), 6.63 (1H, d, J=8.0Hz), 6.94-6.98 (2H, m), 7.23 (2H, d, J=8.4Hz), 7.29-7.45 (5H, m), 7.52 (2H, brs), 7.97 (1 H, d, J=8.0Hz), 8.96 (1 H, t, J=6.0Hz).

According to the analysis of related databases, 22171-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, belongs to ethers-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. Computed Properties of C13H10F3NO

N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide. (1b-1) To a solution of 4-(4-trifluoromethylphenoxy)aniline (15.18 g, 60 mmol) and pyridine (7.2 mL, 90 mmol) in dried CH2Cl2 (100 mL) under N2 at 0 C. was added methanesulfonyl chloride (5.22 mL, 66 mmol) dropwise. The mixture was stirred at 0 C. for 1 h and was then poured into CH2Cl2/H2O (100 mL/100 mL). 2N HCl(aq) (30 mL) was added into additional funnel. The organic layer was then washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product can be resolidified from Et2O/hexane to give 18.2 g of N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (92%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) delta 7.58 (d, J=9.0 Hz, 2H), 7.30 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 4H), 6.93 (s, 1H, NH), 3.04 (s, 3H); MS (EI, m/z): 331 (M+), 330 (M+-1, 100).

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YANG, Shyh-Ming; Wang, Bingbing; Scannevin, Robert; Rhodes, Kenneth; Lagu, Bharat; Wilson, Lawrence J.; Karnachi, Prabha; Murray, William V.; US2008/85893; (2008); A1;,
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