* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With toluene-4-sulfonic acid; sodium nitrite In water; acetonitrile at 5℃; for 1 h; Stage #2: With potassium iodide In water; acetonitrile
General procedure: The mixture of intermediate Bn-2 (1 eq.), PTSA*H20 (i72.5 g, 3 eq) inAcetonitrile (224 ml, 1.3 M) was cooled to 5° C. using a ice bath. NaNO2 (41 .7 g, 2 eq.) in 240 ml water was added dropwise. Afier the addition was finished, the mixture was kept at 5° C. for i hr. The resulting diazonium salt was treated slowly with KI (iOO g, 2 eq.) in 300 ml watet After the completion of the reaction, the residue was extracted with EtOAc and the combined organic layer was washed with a iOpercent Na2SO3(0q) and then dried over Na2504. The organic layer was concentrated under reduced pressure afier filtration. The crude mixture was purified by silica-gel column chromatography to obtain intermediate Bn.
56.5%
Stage #1: With hydrogenchloride In water at 0℃; for 1 h; Stage #2: With potassium iodide In water at 20℃; for 5 h;
1L into a round bottom flask 2-phenoxyaniline (25.0, 0.135mol) and hydrochloric acid, 30ml, 150ml water, cooled to 0 degrees and the mixture was stirred for 1 hour. After the addition the reaction mixture of sodium (11.2g, 0.162mol) in 75ml aqueous solution of the same temperature and the mixture was stirred for one hour. Potassium iodide (44.8g, 0.270mol) and note the temperature of the reaction solution was added dropwise not exceed 5 ° was added dropwise to 75ml of an aqueous solution. Stirred for 5 hours at room temperature after the completion of the reaction haejugo After washing with sodium sayi oh sulfate aqueous solution was extracted with ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure and purified by column chromatography to obtain a intermediate 5-a> (22.6g, 56.5percent)
56.5%
Stage #1: With hydrogenchloride In water at 0℃; for 1 h; Stage #2: at 0℃; for 1 h; Stage #3: With potassium iodide In water at 20℃; for 5 h;
1L round bottom flask reactor2-phenoxy aniline (25.0, 0.135mol)And hydrochloric acid 30ml,Add water to 150ml and cooled to 0 degreesIt was stirred for 1 hour. After dropping a sodium nitro discrete (11.2g, 0.162mol) in 75ml aqueous solution even on the same it was stirred for 1 hour.Potassium iodide (44.8g, 0.270mol)The temperature of the reaction solution, 75ml of an aqueous solution Do not exceed 5 ° and added dropwise. After stirring for 5 hours at room temperature haejugo complete reaction after washing with sodium thiosulfate aqueous solution with ethyl acetate and waterIt was extracted. The organic layer was concentrated under reduced pressure and separated by column chromatography to give the (22.6g, 56.5percent).
56.5%
Stage #1: With hydrogenchloride In water at 0℃; for 1 h; Stage #2: With sodium nitrite In water at 0℃; for 1 h; Stage #3: With potassium iodide In water at 0 - 20℃; for 5 h;
In a 1 L round bottom flask reactor 2-Phenoxyaniline (25.0, 0.135 mol), hydrochloric acid (30 ml) and water (150 ml) were added and the mixture was cooled to 0 ° C and stirred for 1 hour. 75 ml of an aqueous solution of sodium nitrite (11.2 g, 0.162 mol) was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour. When 75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, the temperature of the reaction solution was dropped so that the temperature did not exceed 5 ° C. After stirring for 5 hours at room temperature, the reaction mixture was washed with an aqueous solution of sodium cyanosulfate and extracted with ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure, followed by separation and purification by column chromatography to obtain Intermediate 5-a. (22.6 g, 56.5percent).
56.5%
Stage #1: With hydrogenchloride In water at 0℃; for 1 h; Stage #2: With sodium nitrite In water for 1 h; Stage #3: With potassium iodide In water at 5 - 20℃; for 5 h;
2-phenoxyaniline (25.0, 0.135 mol) and 30 ml of hydrochloric acid were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 ° C and stirred for 1 hour.75 ml of an aqueous solution of sodium nitrite (11.2 g, 0.162 mol) was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour.When the aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, the temperature of the reaction solution was prevented from exceeding 5 ° and dropping.The mixture was stirred at room temperature for 5 hours and washed with an aqueous sodium thiosulfate solution after completion of the reaction, followed by extraction with ethyl acetate and water.The organic layer was separated and concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate 5-a (22.6 g, 56.5percent).
56.5%
Stage #1: With hydrogenchloride In water at 0℃; for 1 h; Stage #2: With sodium nitrite In water at 0℃; for 1 h; Stage #3: With potassium iodide In water at 5 - 20℃; for 5 h;
In a 1 E round bottom flask reactor, a mixture of 2 phenoxyaniline (25.0, 0.135 mol), HC1 (30 ml), and water (150 ml) was cooled to 0° C. and stirred for 1 hr. At the same temperature, an aqueous solution (75 ml) of sodium nitrite (11.2 g, 0.162 mol) was added and then stirred for 1 hr. An aqueous solution (75 ml) of potassium iodide (44.8 g, 0.270 mol) was dropwise added, taking care not to increase the temperature of the reaction solution above 5° C. Stirring was continued for 5 irs at room temperature, and after completion of the reaction, the reaction mixture was washed with an aqueous sodium thiosulfate solution and extracted with ethyl acetate and watet The organic layer was separated and concentrated in a vacuum. Purification through colunm chromatography gave Intermediate 5-a (22.6 g, 56.5percent).
Reference：
[1] Chemistry - A European Journal, 2014, vol. 20, # 39, p. 12553 - 12558
[2] Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1537 - 1555
[3] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3286 - 3291
[4] Patent: US2018/155312, 2018, A1, . Location in patent: Paragraph 0087; 0093-0095
[5] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3775 - 3778
[6] Macromolecules, 2010, vol. 43, # 24, p. 10355 - 10365
[7] European Journal of Organic Chemistry, 2006, # 20, p. 4676 - 4684
[8] Patent: KR2015/130206, 2015, A, . Location in patent: Paragraph 0612-0617
[9] Patent: KR2016/13678, 2016, A, . Location in patent: Paragraph 0429-0435
[10] Patent: KR2017/86011, 2017, A, . Location in patent: Paragraph 0468-0474
[11] Patent: CN107207454, 2017, A, . Location in patent: Paragraph 0349; 0350; 0351; 0353; 0354
[12] Patent: US2017/342318, 2017, A1, . Location in patent: Paragraph 0164; 0165
[13] Journal of the Chemical Society, 1932, p. 281,282
[14] Journal of the Chemical Society, 1931, p. 137,144
[15] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10317 - 10323[16] Angew. Chem., 2015, vol. 127, p. 10457 - 10461,5
[17] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7861 - 7870
2
[ 615-42-9 ]
[ 108-95-2 ]
[ 34883-46-0 ]
Yield
Reaction Conditions
Operation in experiment
42%
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid In acetonitrile at 80℃; for 24 h;
General procedure: To a screw-capped vial (4-mL) were added Cs2CO3 (1.0 mmol, 325 mg), Cu2O (0.005 mmol, 0.7 mg), 1H-imidazole-4-carboxylic acid (0.01 mmol, 1.1 mg) and acetonitrile (0.25 mL). The vial was sealed with septum and allowed to stir for a while; the iodoarene (0.5 mmol) and phenol (0.6 mmol) were then injected into the reaction mixture via a syringe. The septum was removed, and the vial was sealed with a screw cap. The reaction mixture was stirred at 80 oC for 24 h. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 3a-v were obtained according to this procedure. The known structures were characterized by the 1H NMR and 13C NMR of reported literatures.1-3 Spectral data, 1H NMR and 13C NMR spectra for all the new compounds are listed below.
Reference：
[1] Chemistry - A European Journal, 2017, vol. 23, # 53, p. 13249 - 13258
14
[ 71-43-2 ]
[ 101-84-8 ]
[ 34883-46-0 ]
Reference：
[1] Chemistry - A European Journal, 2017, vol. 23, # 53, p. 13249 - 13258
15
[ 101-84-8 ]
[ 34883-46-0 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 15, p. 1969 - 1974
16
[ 533-58-4 ]
[ 1483-73-4 ]
[ 34883-46-0 ]
Reference：
[1] Journal of Organic Chemistry, 1964, vol. 29, p. 3396 - 3398
17
[ 96379-65-6 ]
[ 7553-56-2 ]
[ 34883-46-0 ]
[ 13121-86-3 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1963, p. 681 - 689
[3] Poc. Chem. Soc., 1963, p. 51 - 51
[4] , Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.11, page 339 - 345,
18
[ 121-43-7 ]
[ 34883-46-0 ]
[ 108238-09-1 ]
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 38, p. 12313 - 12317[2] Angew. Chem., 2018, vol. 130, # 38, p. 12493 - 12497,5
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid; In acetonitrile; at 80℃; for 24h;
General procedure: To a screw-capped vial (4-mL) were added Cs2CO3 (1.0 mmol, 325 mg), Cu2O (0.005 mmol, 0.7 mg), 1H-imidazole-4-carboxylic acid (0.01 mmol, 1.1 mg) and acetonitrile (0.25 mL). The vial was sealed with septum and allowed to stir for a while; the iodoarene (0.5 mmol) and phenol (0.6 mmol) were then injected into the reaction mixture via a syringe. The septum was removed, and the vial was sealed with a screw cap. The reaction mixture was stirred at 80 oC for 24 h. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 3a-v were obtained according to this procedure. The known structures were characterized by the 1H NMR and 13C NMR of reported literatures.1-3 Spectral data, 1H NMR and 13C NMR spectra for all the new compounds are listed below.
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