Category: 13321-74-9

Application of 13321-74-9, These common heterocyclic compound, 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, 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.

General procedure: A flask containing LiCl (980 mg,23.1 mmol), 2-bromo-4-fluoroanisole (1.0 mL, 7.7 mmol), DCMA (1.8 mL,8.4 mmol) and ethyl 3-ethoxyacrylate (3.3 mL, 23 mmol) in 1,4-dioxane(20 mL) was degassed by passing a stream of nitrogen through the mixturefor 10 min. Bis(tri-t-butylphosphine) palladium(0) (166 mg, 0.32 mmol) wasadded, and reaction mixture was heated at reflux under nitrogen for 16 h. Thebrown mixture was then cooled and partitioned between ethyl acetate andwater. The layers were separated, and the organic layer was washedsequentially with aqueous NH4Cl and brine, followed by drying over Na2SO4.The mixture was filtered, and the filtrate was concentrated under reducedpressure to give an oil which was purified by flash chromatography on silica(40 g, 10-50% ethyl acetate in heptane) to afford 22c as an orange oil (1.93 g,92%) as an inseparable mixture of E- and Z-isomers: 1H NMR (CDCl3, 500 MHz)alkene protons d: 5.21, 5.33 ppm (1:1 ratio); LCMS (ES): 269.2 (MH). HRMSCalcd for C14H17FO: 269.1184. Found: 269.1196.

The synthetic route of 13321-74-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kohrt, Jeffrey T.; Conn, Ed; Maguire, Robert; Wright, Stephen W.; Singer, Robert; Tetrahedron Letters; vol. 54; 51; (2013); p. 7065 – 7068;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 13321-74-9, 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. 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 1-bromo-2,5-dimethoxy-4-methylbenzene (12) (1.98 g, 8.58 mmol) and (R)-3-acryloyl-4-phenyloxazolidin-2-one (13) (1.86 g, 8.58 mmol) in MeCN/H2O (10:1, 40 mL) were added Pd(OAc)2 (192.58 mg, 0.86 mmol), (o-tol)3P (522 mg, 1.7 mmol), and Et3N (2.391 mL, 0.017 mmol) at rt, and allowed to warm to 80 C. After being stirred at the same temperature for 2 h, the resultant mixture was added water and CH2Cl2 and then extracted with CH2Cl2. The combined extracts were washed with brine, the residue upon workup was chromatographed on silica gel with hexane/AcOEt (4:1 v/v) as a eluent to give a enone 5 (2.564 g, 81%) as a yellow solid; inlMMLBox -5.17 (c 0.95 in CHCl3); mp 55.5-59.5 C; IR (neat) 2958, 1781, 1705, 1505, 1465, 1384, 1209, 1045 cm-1; 1H NMR (400 MHz, CDCl3) delta 2.24 (3H, s), 3.82 (3H, s), 3.82 (3H, s), 4.31 (1H, dd, J=8.8 and 4.0 Hz), 4.73 (1H, t, J=8.8 Hz), 5.57 (1H, dd, J=8.8 and 4.0 Hz), 6.72 (1H, s), 7.02 (1H, s), 7.30-7.39 (5H, m), 7.93 (1H, d, J=16.0 Hz), 8.12 (1H, d, J=16.0 Hz); 13C NMR (100 MHz, CDCl3) delta 16.7 (CH3), 55.8 (CH3), 56.0 (CH3), 57.8 (CH3), 69.8 (CH2), 109.8 (CH), 114.4 (CH), 115.7 (CH), 121.1 (Cq), 125.9 (CH), 128.5 (CH), 129.0 (CH), 131.8 (Cq), 139.3 (Cq), 142.0 (CH), 151.7 (Cq), 153.0 (Cq), 153.9 (Cq), 165.2 (Cq); HRMS (ESI) calcd for C21H21NO5Na [M+Na]+ 390.1317, found 390.1310.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,5-dimethoxytoluene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Miyawaki, Akari; Osaka, Mayu; Kanematsu, Makoto; Yoshida, Masahiro; Shishido, Kozo; Tetrahedron; vol. 67; 35; (2011); p. 6753 – 6761;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, molecular formula is C9H11BrO2, 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: 4-Bromo-2,5-dimethoxytoluene

General procedure: NaOt-Bu (0.240 g, 2.5 mmol), Pd(OAc)2 (0.006 g, 0.025 mmol) and [HPt-Bu3][BF4] (0.010 g, 0.035 mmol) were suspended in toluene (3 ml) in a 5 ml microwave vial. The appropriate 2-chloroaniline (0.50 mmol) and aryl bromide (0.50 mmol) were then added and the vial sealed. The reaction was then heated in the microwave reactor at 160 C for 3 h, allowed to cool, and then quenched by addition of aqueous HCl (2 M, 3 ml). The organic phase was extracted with CH2Cl2 (2×20 ml), dried (MgSO4), then filtered and the solvent removed under reduced pressure. The crude product mixture was then subjected to column chromatography (SiO2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13321-74-9, its application will become more common.

Reference:
Article; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, 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 13321-74-9, category: ethers-buliding-blocks

General procedure: NaOt-Bu (0.240 g, 2.5 mmol), Pd(OAc)2 (0.006 g, 0.025 mmol) and [HPt-Bu3][BF4] (0.010 g, 0.035 mmol) were suspended in toluene (3 ml) in a 5 ml microwave vial. The appropriate 2-chloroaniline (0.50 mmol) and aryl bromide (0.50 mmol) were then added and the vial sealed. The reaction was then heated in the microwave reactor at 160 C for 3 h, allowed to cool, and then quenched by addition of aqueous HCl (2 M, 3 ml). The organic phase was extracted with CH2Cl2 (2×20 ml), dried (MgSO4), then filtered and the solvent removed under reduced pressure. The crude product mixture was then subjected to column chromatography (SiO2).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 13321-74-9,Some common heterocyclic compound, 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, molecular formula is C9H11BrO2, 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-5-methylcyclohexa-2,5-diene-1,4-dione (23). To a solution of toluquinol (1) (2.5 g, 20.14mmol,1.0 equiv.) in acetone (15 mL) was added K2CO3 (14 g, 100.70 mmol, 5.0 equiv.) and Me2SO4 (5.7 mL,60.41 mmol, 3.0 equiv.) and the reaction mixture was stirred for 3 h. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O. The organic phasewas washed with brine, dried over MgSO4, filtered, and the solvent removed under reduced pressureto obtain the corresponding dimethoxy derivative (~20 mmol), which was used in the next stepswithout purification. To a solution of the dimethoxy derivative obtained above (~20 mmol) and NaOAc(3.3 g, 40.28 mmol, 2.0 equiv.) in AcOH (20 mL) was added bromine (1.2 mL, 2.15 mmol, 1.1 equiv.)over 25 min and, after the addition, the reaction mixture was stirred for 1 h. Then, the reaction mixturewas quenched by a slow addition of a saturated aqueous NaHCO3 solution at 0 C. The aqueousphase was then extracted with EtOAc and the organic phase washed with brine, dried over MgSO4,ltered, and the solvent removed under reduced pressure to obtain the corresponding bromo derivative(~20 mmol), which was used in the next step without purication. The bromo derivative obtainedabove (~20 mmol) was dissolved in CH3CN (35 mL). Then, CAN (28 g, 50.34mmol, 2.5 equiv.) and H2O(20 mL) were added and the reaction mixture was stirred for 1 h at 25 C. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O twice. The combinedorganic phases were washed with brine, dried over MgSO4, filtered, and the solvent removed underreduced pressure. The residue was purified by flash column chromatography (silica gel, 1% EtOAc inhexanes) to obtain compound 23 (1.5 g, 37% over 3 steps) as an orange solid [13]: Rf = 0.45 (silica gel,20% EtOAc in hexanes); 1H NMR (400 MHz, CDCl3) delta 7.29 (s, 1 H), 7.26 (s, 2 H), 2.08 (d, J = 1.6 Hz,3 H); 13C NMR (100 MHz, CDCl3) delta 185.1, 179.5, 146.5, 138.1, 137.5, 132.6, 15.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,5-dimethoxytoluene, its application will become more common.

Reference:
Article; Cheng-Sanchez, Ivan; Torres-Vargas, Jose A.; Martinez-Poveda, Beatriz; Guerrero-Vasquez, Guillermo A.; Medina, Miguel Angel; Sarabia, Francisco; Quesada, Ana R.; Marine Drugs; vol. 17; 9; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem