Category: 112970-44-2

Reference of 112970-44-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112970-44-2 name is 2-Bromo-3-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A dry round-bottom flask with a reflux condenser was charged with 2-bromo-3-methoxyanilin (1.00 g, 4.95 mmol), KHMDS(32 mg, 0.16 mmol, 0.03 eq), BrettPhos Pd G1 Methyl-t-Butyl Ether adduct (118 mg, 0.15 mmol, 0.03 eq) and Cs2CO3 (3.22 g,9.88 mmol, 2.0 eq). The system was sealed by a rubber septum before air was removed under reduced pressure and replaced by argon (repeated 3 times). Anhydrous toluene (20 mL) was transferred to the flask and the resulting orange colored suspension gradually warmed up to reflux and left stirring for 24 h. The heating was removed and the crude mixture was cooled to reach rt . Thereaction mixture was filtered through a funnel of Celite and undissolved material washed with DCM until no yellow solution came through the funnel. The resulting crude mixture was dry-loadedon silica and purified by flash column chromatography on silicagel (1:7 EtOAc/DCM as eluent) affording 468 mg (79%) of the yellow solid. Rf: 0.51 (100% EtOAc). 1H NMR (400 MHz, CDCl3) d7.99 (dd, J = 8.9, 1.1 Hz, 2H), 7.74 (dd, J = 8.9, 7.6 Hz, 2H), 7.09(dd, J = 7.6, 1.1 Hz, 2H), 4.17 (s, 6H). 13C NMR (101 MHz, CDCl3) d155.1, 143.2, 137.0, 130.3, 122.2, 107.0, 56.6. HRMS (EI): Exactmass calculated for C14H12N2O2: 240.0899, found 240.0894(1.8 ppm). 1H- and 13C NMR data are in accordance with published literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Viktorsson, Elvar Oern; Melling Gr°the, Bendik; Aesoy, Reidun; Sabir, Misbah; Snellingen, Simen; Prandina, Anthony; H°gmoen ?strand, Ove Alexander; Bonge-Hansen, Tore; D°skeland, Stein Ove; Herfindal, Lars; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2285 – 2293;,
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Reference of 112970-44-2, The chemical industry reduces the impact on the environment during synthesis 112970-44-2, name is 2-Bromo-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

A solution of the bromoaniline (208 mmol) in 50% hydrochloric acid (40 mL) was added to a solution of trichloroacetaldehyde hydrate (312 mmol) and sodium sulfate (967 mmol) in water (450 mL) and the reaction mixture was maintained for 1 h. A solution of hydroxylamine hydrochloride (793 mmol) in water (240 mL) was added and the reaction mixture was heated at 60 C. for 2 h. The aqueous layer was decanted and the residual red oil, which solidifies upon standing, was purified by chromatography (6/6/1 petroleum ether/dichloromethane/ethyl acetate) to provide the alpha-oxime amide in 29% yield as a light yellow solid.

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, 2-Bromo-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok; US2007/78147; (2007); A1;,
Ether – Wikipedia,
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112970-44-2, name is 2-Bromo-3-methoxyaniline, 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. HPLC of Formula: C7H8BrNO

35% HCl (3 mL) and ice (3 g) were added to 2-bromo-3-methoxyphenylamine (0.83 g, 4.11 mmol) obtainedin Step A, and cooled to 0-5C. NaNO2 (0.31 g, 4.52 mmol)/H2O (2 mL) solution was slowly added thereto, and themixture was stirred at 0-5C for 20 minutes. Pre-prepared KI (6.82 g, 41.1 mmol)/H2O (10 mL) solution was slowly addeddropwise to the reaction solution, and the reaction was carried out at room temperature for 12 hours. After terminationof the reaction, NaOH solution was added thereto, and the reaction solution was extracted with DCM. The organic layerwas washed with saturated NaHCO3 aqueous solution and water. The extracted organic layer was concentrated underreduced pressure and purified by column chromatography (eluent, EtOAc/Hex = 1/10) to obtain the title compound (0.88g, 68 %).1H NMR (500 MHz, CDCl3) delta 7.48(d, 1H), 7.00(dd, 1H), 6.85(d, 1H), 3.87(s, 3H)

The synthetic route of 112970-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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Electric Literature of 112970-44-2, A common heterocyclic compound, 112970-44-2, name is 2-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 2-bromo-3-methoxyaniline B4 (0.79 g; 3.9 MMOL) in MEOH (7.6 mL) was added dimethyl acetylene dicarboxylate A3 (0.53 mL; 4.3 MMOL) dropwise at 0 C (caution: reaction is exothermic.). The solution was heated overnight at reflux and worked-up. The MEOH was evaporated and the crude product dried under high vacuum to afford a red gum, purified by flash column chromatography (1: 30 ultra pure silica gel, 230-400 mesh, 40-60 mm, 60 angstroms; 4: 1 hexane/EtOAc) to afford adduct B5 (86 %; 1.16 g) as a pale yellow solid. MS 344. 0 (MH) + ; Homogeneity by HPLC (TFA) 220 nm: 72%.

The synthetic route of 112970-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO KG; WO2004/103996; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 112970-44-2, 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 112970-44-2 as follows.

Step 2. Synthesis of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroacetamide (C24) Trifluoroacetic anhydride (3.0 mL, 22 mmol) was added to a solution of 2-bromo-3-methoxyaniline (C23) (2.57 g, 10.77 mmol) and triethylamine (4.51 mL, 32.3 mmol) in dichloromethane (30 mL) at -78 C. The reaction was allowed to warm to room temperature and stirring was continued for 18 hours, whereupon the mixture was poured into water (40 mL) and extracted with dichloromethane (2*20 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% methyl tert-butyl ether in hexanes) afforded the title compound as a colorless solid. Yield: 2.97 g, 9.96 mmol, 92%. GCMS m/z 297, 299 (M+). 1H NMR (400 MHz, CDCl3) delta 3.94 (s, 3H), 6.81 (dd, J=8.4, 1.2 Hz, 1H), 7.35 (dd, J=8.4, 8.3 Hz, 1H), 7.97 (dd, J=8.3, 1.3 Hz, 1H), 8.59 (br s, 1H).

According to the analysis of related databases, 112970-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O’Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 112970-44-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112970-44-2 name is 2-Bromo-3-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A dry round-bottom flask with a reflux condenser was charged with 2-bromo-3-methoxyanilin (1.00 g, 4.95 mmol), KHMDS(32 mg, 0.16 mmol, 0.03 eq), BrettPhos Pd G1 Methyl-t-Butyl Ether adduct (118 mg, 0.15 mmol, 0.03 eq) and Cs2CO3 (3.22 g,9.88 mmol, 2.0 eq). The system was sealed by a rubber septum before air was removed under reduced pressure and replaced by argon (repeated 3 times). Anhydrous toluene (20 mL) was transferred to the flask and the resulting orange colored suspension gradually warmed up to reflux and left stirring for 24 h. The heating was removed and the crude mixture was cooled to reach rt . Thereaction mixture was filtered through a funnel of Celite and undissolved material washed with DCM until no yellow solution came through the funnel. The resulting crude mixture was dry-loadedon silica and purified by flash column chromatography on silicagel (1:7 EtOAc/DCM as eluent) affording 468 mg (79%) of the yellow solid. Rf: 0.51 (100% EtOAc). 1H NMR (400 MHz, CDCl3) d7.99 (dd, J = 8.9, 1.1 Hz, 2H), 7.74 (dd, J = 8.9, 7.6 Hz, 2H), 7.09(dd, J = 7.6, 1.1 Hz, 2H), 4.17 (s, 6H). 13C NMR (101 MHz, CDCl3) d155.1, 143.2, 137.0, 130.3, 122.2, 107.0, 56.6. HRMS (EI): Exactmass calculated for C14H12N2O2: 240.0899, found 240.0894(1.8 ppm). 1H- and 13C NMR data are in accordance with published literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Viktorsson, Elvar Oern; Melling Gr°the, Bendik; Aesoy, Reidun; Sabir, Misbah; Snellingen, Simen; Prandina, Anthony; H°gmoen ?strand, Ove Alexander; Bonge-Hansen, Tore; D°skeland, Stein Ove; Herfindal, Lars; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2285 – 2293;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 112970-44-2, A common heterocyclic compound, 112970-44-2, name is 2-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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.

A solution of Intermediate iSA (3.25 g, 16.09 mmol) and potassium 0-ethyl carbonodithioate (6.45 g, 40.2 mmol) in DMF (20 mL) was heated at 135 C under argon for 6.0 h. HPLC and LCMS indicated a completion of the reaction. The mixture was cooled to room temperature, diluted with 20 mL water, followed by addition of 30 mL 1.0 N HC1. The precipitate formed was collected by filtration, washed with water, dried under vacuum and then chased with toluene (3X) to yield Intermediate 15B (3.1 g, 15.71 mmol, 98 % yield) as a brown solid. It was used for the next step without further purification. ?H NMR (500MHz, DMSO-d6) 13.77 (br. s., 1H), 7.38 (t, J=8.1 Hz, 1H), 6.94 (t, J=8.1 Hz, 2H), 3.91 (s, 3H); LC-MS: method A, RT = 1.63 mm, MS (ESI) m/z:198.0(M+H).

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 of 112970-44-2,Some common heterocyclic compound, 112970-44-2, name is 2-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 2-bromo-3-aminoanisole 2b4 (750mg, 3.7mmol, 1eq) was added imidate2g2 (0.73g, 3.7mmol, 1eq) in ethanol (7 ml) under a N2 atmosphere. The mixture wasstirred at R.T. for 24 hrs at which point the reaction was concentrated and purifieddirectly on a silica gel column (eluent: EtOAc/Hexanes (1:9)) to afford adduct 2o1(1.12g, 88%) as a pale yellow oil. MS: 344 (M + H)+ and 346 (MH + 2)+.

The synthetic route of 112970-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 112970-44-2, name is 2-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

A mixture of compound 58-1 (200 mg, 989.86 umol, 1 eq.), compound 58-1 (243.76 mg, 1.19 mmol, 1.2 eq.) and EDCI (284.64 mg, 1.48 mmol, 1.5 eq.) in pyridine (3 mL) was stirred at 20 C for 12 hours. The mixture was diluted with EtOAc (30 mL), washed with 1 N hydrochloric acid solution (20 mL*3) dried with sodium sulfate, filtered and concentrated. The residue was purified by prepTLC (PE:EA = 3:1) to give compound 58-2 (150 mg,, yield: 38 %) as brown oil. LCMS: 391.1 [M+ 11

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; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem