Category: 52807-27-9

Application of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.

Add 4-chloro-2-iodo-anisole (10.9 mL, 75.0 mmol), trimethylsilyl acetylene (15.9 mL, 112.5 mmol), copper (I) iodide (0.29 g, 1.5 mmol), and THF (225 ML, anhydrous) to a dry round bottom flask. Add diisopropylamine (22.1 mL, 157.5 mmol) and dichlorobis (triphenylphosphine) palladium (II) (1.58 g, 2.3 mmol) and stir the mixture at room temperature under N2 overnight. Quench reaction with water and extract with EtOAc (x2). Wash combined organic layers with brine, dry over MGS04 and concentrate to get 24 g of a black oil. Adsorb on SI02 and purify the residue by flash chromatography on silica gel eluting with 0-3% ETOAC/HEXANES to afford (5-chloro-2-methoxy- phenylethynyl) -trimethylsilane (13.7 g, 76%). Add a solution of potassium hydroxide (3. 28 g, 58. 5 mmol) in water (30 mL) dropwise over 25 minutes to a stirred solution of (5-chloro-2-methoxy-phenylethynyl)- trimethylsilane (13.7 g, 57.4 mmol) in methanol (275 mL) and stir at room temperature for 2 hours. Concentrate, add brine to residue, and extract with EtOAc (x2). Dry organic layer over MGS04 and concentrate to get 13 g of a black oil. Adsorb on Si02 and purify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes to afford the title compound (8. 98 g, 94%).

The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19184; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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 4-chloro-2-iodo-1-methoxybenzene (500mg, 1.86mmol), the compound of preparation 28, (316mg, 1.86mmol), copper iodide (18mg, 0.09mmol), potassium carbonate (515mg, 3.72mmol), and ethylene glycol (208muL, 3.72mmol) in 2-propanol (5mL) was heated at 80 0C for 24h. The mixture was cooled to rt and the solvent was removed in vacuo. The residue was partitioned between EtOAc (2OmL) and water (2OmL). The phases were separated and the organic phase was dried over magnesium sulfate and the solvent was removed in vacuo to give the crude residue. Purification by column chromatography on silica gel using pentane:ethyl acetate (100:0-90:10) as eluent afforded the desired product as a white solid, 321 mg (56%)1H NMR (400 MHz, CDCI3) delta 3.80 (3H, s), 6.90 (1 H, d), 7.20 (1 H, s), 7.36 (1 H, m), 7.40 (3H, m).

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

Reference:
Patent; PFIZER LIMITED; WO2006/67587; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 52807-27-9, These common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, 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 mixture of the aryl halide (0.6 mmol), arylboronic acid (2.5 equiv), Mo(CO)6 (1.5 equiv), DIPEA (3.0 equiv), palladacycle 1 (1 mol % Pd), and water (1.0 mL) was heated in a pressure tube at 140 C under microwave irradiation. The reaction was monitored by TLC. When the reaction has completed, the reaction mixturewas cooled to room temperature, poured into EtOAc (20 mL) and washed successively with water (310 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude product was then purified by column chromatography to give pure 4.

The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ang, Wei Jie; Lo, Lee-Chiang; Lam, Yulin; Tetrahedron; vol. 70; 45; (2014); p. 8545 – 8558;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.

Add to a solution of 4-chloro-2-iodoanisole (10 g, 37.24 mmol) in 1,4-dioxane (50 mL) is 2-thiopheneboronic acid (5.71 g, 44.66 mmol), (2-dicyclohexylphosphino)-2′- methylbiphenyl (2.71 g, 7.44 mmol), palladium acetate (0.418 g, 1.86 mmol) and potassium fluoride (6.49 g, 111.7 mmol). Stir at 95 C for 18 h, cool to room temperature, filter through a filtering agent and wash with ethyl acetate (400 mL). Wash organic layer with water (3 x 100 mL), saturated aqueous sodium chloride (1 x 100 mL), dry over sodium sulfate, filter, concentrate and purify (HPLC, eluting with hexanes) to give the titled compound as an oil (5.4g). HRMS m/z Calculated: 225.0141; Found: 225.0132

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/100301; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.

4-Chloro-2-iodophenol; 109.4g (0.436mol) of boron tribromide were added over 10 minutes to a stirred solution of 9Og (0.335mol) of 4-chloro-2-iodoanisole in dichloromethane (900ml) at -780C under nitrogen. Cooling was removed and allowed to warm to room temperature and stirred for 5 hours. Poured onto ice and diluted with a further 800ml of water. The organic phase was separated, the aqueous extracted with dichloromethane and the combined organics washed with saturated sodium bicarbonate, dried and evaporated to give 84.87g of off- white solid; Sodium 6-r(5-chloro-2-fr(4-chloro-2-fluorophenyl)methvnoxy)phenyl)methvn-2- pyridinecarboxylate (Alternative route 2); 4-Chloro-2-iodophenol; Boron tribromide (1349g) was added to a solution of 4-chloro-2-iodoanisole (1025g) in dichloromethane (10.3L) under nitrogen at such a rate that the temperature remained at 0- 5C The solution was then warmed to 200C and stirred for c. 19h until the reaction was complete by HPLC. This organic solution was added to water (8.2L) and the mixture was cooled to 5C to 10C. DCM (770ml) was added and the resuting biphasic mixture was then stirred at 50C for 15 min before being warmed to 220C and then finally stirred at 22C for 20 min before separating the phases. The separated organic phase was washed with aqueous saturated sodium bicarbonate (3.1L), water (3.1L) and then evaporated on a Buchi to give the title compound. (963.6g)

The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/66968; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52807-27-9, A common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 52807-27-9, 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. 52807-27-9, name is 4-Chloro-2-iodoanisole belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under a nitrogen atmosphere, tris (dibenzylideneacetone) dipalladium (2.29 g, 2.5 mmol) , 1, V -bis (diphenylphosphi.no) ferrocene (2.11 g, 5 mmol) , sodium tert-butoxide (6.73 g, 70 mmol) and toluene (150 ml) were mixed. To this solution, 2-amino-3-bromo-5-methylpyridine (9.82 g, 52.5 mmol), 4-chloro-2-iodo-l-methoxybenzene (13.42 g, 50 mmol) and toluene (100 ml) were added. The mixture was stirred at an internal temperature of 9O0C for 2 hours. The reaction solution was cooled to room temperature, and IN hydrochloric acid (150 ml) was added thereto. The insoluble was filtered off and washed twice with toluene (50 ml) . The organic layer was separated and washed sequentially, once with 5N aqueous sodium hydroxide solution (50 ml) and twice with water (50 ml) . The organic layer was concentrated under reduced pressure, ethanol/acetone (4/1, 30 ml) was added to the concentrate, and the crystals were collected by filtration. The crystals were washed three times with ethanol/acetone (4/1, 15 ml) , and dried under reduced pressure at 50C, to yield the title compound (12.88 g) (yield 78.6%).1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.23 (3H, s) , 3.92 (3H, s), 6.77 (IH, d, J = 8.6 Hz), 6.87 (IH, dd, J = 2.5 Hz, 8.6 Hz), 7.59 (IH, d, J = 1.5 Hz), 7.75 (IH, brs) , 8.05 (IH, d, J = 1.0 Hz), 8.69 (IH, d, J = 2.5 Hz). 13C-NMR (CDCl3, TMS, 75 MHz) delta (ppm): 17.1, 56.2, 106.8, 110.4, 117.1, 120.1, 125.4, 126.0, 131.2, 140.9, 146.0, 146.3, 149.3.Mass analysis (Ci3Hi2N2OBrCl) Theoretical value: 326 Measured value: 327 [M+H]+Elemental analysis (Ci3Hi2N2OBrCl)Theoretical value: C, 47.66; H, 3.69; N, 8.55; Br, 24.39; Cl , 10 . 82Measured value: C, 47.94; H, 3.62; N, 8.68; Br, 24.36; Cl, 10.86Melting point: 140.2C

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, 4-Chloro-2-iodoanisole, other downstream synthetic routes, hurry up and to see.

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. 52807-27-9, name is 4-Chloro-2-iodoanisole, A new synthetic method of this compound is introduced below., Product Details of 52807-27-9

EXAMPLE 37A 3′,5-dichloro(1,1′-biphenyl)-2-yl methyl ether A suspension of 4-chloro-2-iodo-1-methoxybenzene (2.5 g, 9.3 mmol) and 3-chlorophenylboronic acid (2.2 g, 13.9 mmol) in a mixture of toluene (10 mL), dioxane (10 mL), and 2N Na2CO3 (10 mL) was treated with tetrakis(triphenylphosphine)-palladium (O) (0.54 g, 0.47 mmol), heated to reflux for 16 hours, cooled to room temperature, and extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20:1 hexanes/ethyl acetate to provide 2.5 g (100%) of the desired product. MS (DCI/NH3) m/z 254 (M+H)+; 1H NMR (CDCl3) delta 7.75-7.23 (m, 6H), 6.91 (d, 1H), 3.80 (s, 3H).

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.

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. 52807-27-9, name is 4-Chloro-2-iodoanisole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6ClIO

Example 5: Synthesis of 1-BICYCLO [2.2. 1] hept-5-en-2-ylmethyl-4- (5-chloro-2-methoxy-phenyl)-2-methyl-piperazine. CH3 Pd2dba3 1 I N (+)-BINAP OMe CNH NaBH (OAc) 3 OMe N I C 3 18-crown-6 SN QCH3 y’J”3 i J N NaOt-Bu/THF H pwave, 80 OC 5 mine [0102] 10 mg (0. 010 eq) PD2DBA3-CHC13, 9. 0 mg (0.015 eq) racemic BINAP, 135 mg (1.4 eq) NAOT-BU, 370 mg (1.4 eq) 18- crown-6 ether and 1.0 mL anhydrous tetrahydrofuran were combined in a microwave vial. 268 mg (1.0 EQ, 1. 0 mmol) 4-Chloro-2- IODOANISOLE was added, followed by 120 mg (1.2 eq) racemic 2- methylpiperazine. The vial was flushed with nitrogen prior to being microwaved at 80C for 5 minutes. The reaction mixture was diluted with 1.0 mL DMSO: methanol (1 : 1) and centrifuged (4, 000 rpm, RT, 8 min). The supernatant was filtered and purified by reverse-phase HPLC (2-99% CH3CN in 0. 085% TFA (AQ), 50 ML/MIN, 2.0 mL injected). Yield = 50 mg (14%) of a light brown oil (isolated as the mono-TFA salt); [0103] 1H-NMR (400 MHZ, DMSO-D6) No. 9.14 (br d, J = 8.6 Hz, 1H), 8. 71 (br d, J = 7.8 HZ, 1H), 7. 10 (dd, J = 8.7 HZ, 2. 4 HZ, 1H), 6. 99 (d, J = 8.8 HZ, 1H), 6. 94 (d, J = 2.5 HZ/1H)/3. 80 (S, 3H), 3. 42 (br M, 4H), 3. 17 (M, 1H), 2. 85 (M, 1H), 2. 72 (M, 1H), 1. 25 (d, J = 6.4 HZ, 3H) ; LC/MS retention time (10-99% CH3CN/0. 05% TFA gradient over 5 min): 1.82 min; Theoretical (M+H) + m/z = 241. 1; Found 241.2.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 52807-27-9.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/30188; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com