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Chemical Structure| 696-62-8
Chemical Structure| 696-62-8
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Product Details of [ 696-62-8 ]

CAS No. :696-62-8 MDL No. :MFCD00001056
Formula : C7H7IO Boiling Point : -
Linear Structure Formula :- InChI Key :SYSZENVIJHPFNL-UHFFFAOYSA-N
M.W : 234.03 Pubchem ID :69676
Synonyms :

Calculated chemistry of [ 696-62-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.65
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 2.95
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.062 mg/ml ; 0.000265 mol/l
Class : Soluble
Log S (Ali) : -2.81
Solubility : 0.366 mg/ml ; 0.00156 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.0771 mg/ml ; 0.00033 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 696-62-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 696-62-8 ]

* 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.

  • Upstream synthesis route of [ 696-62-8 ]
  • Downstream synthetic route of [ 696-62-8 ]

[ 696-62-8 ] Synthesis Path-Upstream   1~43

  • 1
  • [ 288-88-0 ]
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  • [ 13423-60-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 51, p. 40628 - 40635
  • 2
  • [ 696-62-8 ]
  • [ 1139-83-9 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
  • 3
  • [ 15226-74-1 ]
  • [ 696-62-8 ]
  • [ 6148-64-7 ]
  • [ 2881-83-6 ]
YieldReaction ConditionsOperation in experiment
89% With 1H-imidazole; palladium diacetate; triethylamine; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; magnesium chloride In tetrahydrofuran at 90℃; for 0.5 h; Microwave irradiation To a stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 molpercent), Xantphos (5 mol percent), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90°C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 25, p. 3525 - 3528
  • 4
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  • [ 172282-33-6 ]
  • [ 5176-27-2 ]
  • [ 198981-85-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 15, p. 2755 - 2761
  • 5
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  • [ 13788-72-2 ]
Reference: [1] Australian Journal of Chemistry, 2011, vol. 64, # 4, p. 454 - 470
  • 6
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  • [ 29558-77-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148
  • 7
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  • [ 52244-70-9 ]
Reference: [1] ChemMedChem, 2016, p. 2024 - 2036
  • 8
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  • [ 802294-64-0 ]
  • [ 1929-29-9 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 70, p. 17697 - 17700
  • 9
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  • [ 5043-54-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935
[2] Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935
  • 10
  • [ 696-62-8 ]
  • [ 42523-29-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935
[2] Organic Letters, 2017, vol. 19, # 5, p. 1140 - 1143
[3] Organic Letters, 2017, vol. 19, # 5, p. 1140 - 1143
  • 11
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  • [ 393-52-2 ]
  • [ 348-52-7 ]
  • [ 100-07-2 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 12
  • [ 124-38-9 ]
  • [ 696-62-8 ]
  • [ 2786-00-7 ]
Reference: [1] Chemische Berichte, 1964, vol. 97, p. 3098 - 3105
[2] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 1010 - 1016
  • 13
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  • [ 2786-00-7 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 346
  • 14
  • [ 109-72-8 ]
  • [ 60-29-7 ]
  • [ 696-62-8 ]
  • [ 2786-00-7 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 346
  • 15
  • [ 696-62-8 ]
  • [ 922-67-8 ]
  • [ 7515-17-5 ]
Reference: [1] Organic letters, 2001, vol. 3, # 20, p. 3111 - 3113
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6341 - 6349
[3] Synthetic Communications, 1998, vol. 28, # 2, p. 327 - 335
[4] Organic Letters, 2013, vol. 15, # 18, p. 4888 - 4891
  • 16
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  • [ 5399-03-1 ]
Reference: [1] Journal of the Chemical Society, 1916, vol. 109, p. 1087
  • 17
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  • [ 5399-03-1 ]
  • [ 52692-09-8 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1000,2595[2] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
  • 18
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  • [ 7697-37-2 ]
  • [ 5399-03-1 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 406
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  • [ 7697-37-2 ]
  • [ 5399-03-1 ]
  • [ 52692-09-8 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1000,2595[2] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
[3] Bulletin de la Societe Chimique de France, 1897, vol. <3> 17, p. 115
  • 20
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YieldReaction ConditionsOperation in experiment
88% With N-Bromosuccinimide; silver nitrate In acetonitrile for 5 h; Reflux General procedure: To a stirred mixture of CH3CN (5 mL) and NBS (1.0 mmol, 0.177 g) at reflux, was added AgNO3 (1.0 mmol, 0.169 g). N,N-Dimethylaniline (1 mmol, 0.126 mL) was then added to the mixture. After 3 h, the mixture was filtered to remove AgBr. The solvent was evaporated and the residue dissolved in CH2Cl2 (10 mL) and washed with aqueous 4percent NaHCO3 (2 .x. 5 mL) to remove N-hydroxysuccinimide from the organic phase. The aqueous phase was separated and the organic phase dried and concentrated. The residue was subjected to column chromatography over silica gel using n-hexane/EtOAc (4:1) as eluent to give 4-nitro- and 2-nitro-N,N-dimethylaniline in 69percent and 16percent yields, respectively.
75% With iodine; silver nitrate; chloro-diphenylphosphine In dichloromethane at 20℃; for 4 h; In a typical experiment: to a flask containing a stirred mixture of Ph2PCl (1.1 mmol, 0.202 mL) and I2 (1.1 mmol, 0.279 g) in CH2Cl2 (5 mL), was added silver nitrate (2.2 mmol, 0.373 g) at room temperature. N,N-Dimethylaniline (2.0 mmol, 0.252 mL) was then added to the reaction mixture. After 10 min, the mixture was filtered to remove precipitated AgCl and AgI. The residue was washed with saturated aqueous Na2CO3 (3 .x. 5 mL) until all the diphenylphosphinic acid was removed from the organic phase. The aqueous phase was separated and the organic phase washed with aqueous Na2S2O3 (2 .x. 5 mL) to remove the excess I2 and then H2O (5 mL), dried, and concentrated. Column chromatography of the residue was performed on silica gel using n-hexane/EtOAc (4:1) as eluent to give pure 2-nitro- and 4-nitro-N,N-dimethylanilines in 15percent and 77percent yields, respectively.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 36, p. 4841 - 4842
[2] Organic Letters, 2017, vol. 19, # 19, p. 5114 - 5117
[3] Tetrahedron Letters, 2011, vol. 52, # 39, p. 5081 - 5082
  • 21
  • [ 696-62-8 ]
  • [ 100-17-4 ]
  • [ 52692-09-8 ]
Reference: [1] Journal of Chemical Research, Synopses, 1995, # 7, p. 284 - 285
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  • [ 52692-09-8 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1000,2595[2] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
  • 23
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  • [ 7697-37-2 ]
  • [ 5399-03-1 ]
  • [ 52692-09-8 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1000,2595[2] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
[3] Bulletin de la Societe Chimique de France, 1897, vol. <3> 17, p. 115
  • 24
  • [ 547-63-7 ]
  • [ 696-62-8 ]
  • [ 6274-50-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With 2,2,6,6-tetramethylpiperidinyl-lithium In toluene at 20℃; for 0.25 h; Glovebox
Stage #2: With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 20℃; Glovebox
General procedure: Inside the glovebox, lithium 2,2,6,6-tetramethylpiperidide (LiTMP, 70.7 mg, 0.48 mmol, 1.2 eq.) was dissolved in toluene (1.5 mL) and carbonyl compound (3, 0.48 mmol, 1.2 eq.) was added. After 15 min of stirring at ambient temperature a solution of Pd(I) iodo dimer (2, 3.5 mg, 0.004 mmol, 1 molpercent for aryl iodides; 17.4 mg, 0.02 mmol, 5 molpercent for aryl bromides) and aryl halide (4, X = I or Br, 0.4 mmol, 1.0 eq.) in toluene (0.5 mL) was added. After 4-18 h of further stirring at ambient temperature (reaction progress was monitored by GCMS), the crude was directly adsorbed onto silica (washing with diethyl ether) and purified by flash column chromatography.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 22, p. 4471 - 4475
  • 25
  • [ 696-62-8 ]
  • [ 62-53-3 ]
  • [ 20440-94-2 ]
YieldReaction ConditionsOperation in experiment
87% With potassium <i>tert</i>-butylate In toluene at 115℃; for 3.5 h; EXAMPLE 5; Amination reaction was carried out in a 50 ml capacity two neck round bottom flask. In a typical experiment, Toluene (23 ml) was charged to the round bottom flask followed by CuI (0.28 mmol), 1,6-bis(diphenylphosphino)hexane (0.28 mmol), aniline (7.85 mmol), p-methoxy iodobenzene (16.48 mmols), and KOt-Bu (23.5 mmol). Reflux condenser was attached to the flask and the round bottom flask was flushed twice with nitrogen to ensure removal of air. Nitrogen balloon was attached to the condenser, to maintain nitrogen atmosphere during the reaction. The round bottom flask was then stirred by magnetic needle and heated to 115° C. in oil bath and the reaction was continued for 3.5 hours. After cooling to room temperature, the reaction solution was filtered to remove the precipitated base and washed with solvent. The product was separated by column chromatography. The isolated yield of N,N-bis(4-methoxyphenyl)aniline was 87percent.
87% With 1,6-bis(diphenylphosphino)hexane; potassium <i>tert</i>-butylate In toluene at 115℃; for 3.5 h; Amination reaction was carried out in a 50 ml capacity two neck round bottom flask. In a typical experiment, Toluene (23 ml) was charged to the round bottom flask followed by CuI (0. 28mmol), 1, 6-bis (diphenylphosphino) hexane (0.28mmol), aniline (7. 85mmol), p- methoxy iodobenzene (16.48mmols), and KOt-Bu (23. 5mmol). Reflux condenser was attached to the flask and the round bottom flask was flushed twice with nitrogen to ensure removal of air. Nitrogen balloon was attached to the condenser, to maintain nitrogen atmosphere during the reaction. The round bottom flask was then stirred by magnetic needle and heated to 115°C in oil bath and the reaction was continued for 3 : 5 hours. After cooling to room temperature, the reaction solution was filtered to remove the precipitated base and washed with solvent. The product was separated by column chromatography. The isolated yield of N, N-bis (4-methoxyphenyl) aniline was 87percent.
74% With potassium <i>tert</i>-butylate In toluene at 115℃; for 3.5 h; EXAMPLE 2; Amination reaction was carried out in a 50 ml capacity two neck round bottom flask. In a typical experiment, Toluene (23 ml) was charged to the round bottom flask followed by CuI (0.28 mmol), Bis(diphenylphosphino)methane (0.28 mmol), aniline (7.85 mmol), p-methoxy iodobenzene (16.48 mmols), and KOt-Bu (23.5 mmol). Reflux condenser was attached to the flask and the round bottom flask was flushed twice with nitrogen to ensure removal of air. Nitrogen balloon was attached to the condenser, to maintain nitrogen atmosphere during the reaction. The round bottom flask was then stirred by magnetic needle and heated to 115° C. in oil bath and the reaction was continued for 3.5 hours. After cooling to room temperature, the reaction solution was filtered to remove the precipitated base and washed with solvent. The product was separated by column chromatography. The isolated yield of N,N-bis(4-methoxyphenyl)aniline was 74percent.
74% With potassium <i>tert</i>-butylate; bis-diphenylphosphinomethane In toluene at 115℃; for 3.5 h; Amination reaction was carried out in a 50 ml capacity two neck round bottom flask. In a typical experiment, Toluene (23 ml) was charged to the round bottom flask followed by Cul (0. 28mmol), Bis (diphenylphosphino) methane (0.28mmol), aniline (7.85mmol), p- methoxy iodobenzene (16.48mmols), and KOt-Bu (23. 5mmol). Reflux condenser was attached to the flask and the round bottom flask was flushed twice with nitrogen to ensure removal of air. Nitrogen balloon was attached to the condenser, to maintain nitrogen atmosphere during the reaction. The round bottom flask was then stirred by magnetic needle and heated to 115°C in oil bath and the reaction was continued for 3.5 hours. After cooling to room temperature, the reaction solution was filtered to remove the precipitated base and washed with solvent. The product was separated by column chromatography. The isolated yield of N, N-bis (4-methoxyphenyl) aniline was 74percent.
70.1% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneInert atmosphere; Reflux Synthesis of N,N-bis(4-methoxyphenyl)aniline. Freshly distilled aniline (4.84 g, 52.0 mmol), />;-iodoanisole (30.4 g, 130.0 mmol), powdered anhydrous potassium carbonate (57.5 g, 416.0 mmol), electrolytic copper powder (13.3 g, 208.0 mmol), and 18-crown-6 (2.75 g, 10.4 mmol) were added to a dry, three necked round bottom flask under nitrogen. The mixture was refluxed in 100 mL o- dichlorobenzene 18 h (during which time some solvent evaporated).. Ethyl acetate (250 mL) was added to the reaction flask. The resulting mixture was filtered to remove copper and organic salts and the solvent was removed under reduced pressure. The product was purified by washing with methanol to yield a tan solid (11.2 g, 70.10Zo)-1H NMR (300 MHz, CDCl3) δ 7.16 (m, 2H), 7.01 (d, J = 9.0 Hz, 4H), 6.78 (d, J = 9.0 Hz, 4H), 6.83 (t, J = 1.5 Hz, 2H), 6.81 (t, J = 1.5 Hz, IH), 3.55 (s, 6H).
70% at 135℃; for 6 h; To a mixture of 4-iodoanisole (0.70 g, 3.00 mmol), t-BuOK (0.34 g, 3.00 mmol), 2,2′-bipyridine (3 mg, 0.02 mmol) and CuI(I) (4 mg, 0.02 mmol) was added toluene (6 mL) and aniline (0.09 mL, 1.00 mmol). The solution was heated and reacted for 6 hours at 135° C. After the reaction was cooled to room temperature, the solid product was filtered off and washed with toluene. The filtrates were combined, and the solvent was removed therefrom to obtain a residue. The residue was purified by Silica Gel Column Chromatography using n-hexane, to give an intermediate product as a yellow solid (0.21 g, 70percent). The intermediate product was identified and assayed, and the result was shown as follows: 1H NMR (400 MHz, CdCl3) δH=7.15 (t, J=7.6 Hz, 2H), 7.03 (d, J=7.6 Hz, 4H), 6.91 (d, J=7.6 Hz, 2H), 6.72-6.88 (m, 5H), 3.77 (s, 12H).
70.1% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 18 h; Inert atmosphere; Reflux Freshly distilled aniline (4.84 g, 52.0 mmol), p-iodoanisole (30.4 g, 130.0 mmol), powdered anhydrous potassium carbonate (57.5 g, 416.0 mmol), electrolytic copper powder (13.3 g, 208.0 mmol), and 18-crown-6 (2.75 g, 10.4 mmol) were added to a dry, three necked round bottom flask under nitrogen. The mixture was refluxed in 100 mL o-dichlorobenzene 18 h (during which time some solvent evaporated). Ethyl acetate (250 mL) was added to the reaction flask. The resulting mixture was filtered to remove copper and organic salts and the solvent was removed under reduced pressure. The product was purified by washing with methanol to yield a tan solid (11.2 g, 70.1percent).
65.6% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In toluene for 12 h; Inert atmosphere; Reflux 4-iodoanisole (7.20 g, 30.76 mmol) and aniline (1.14 mL, 12.49 mmol) were dissolved in a round-bottom flask in 50 mL toluene, and o-phenanthroline (0.45 g, 2.30 mmol), cuprous iodide (0.48 g, 2.52 mmol) and potassium hydroxide (5.60 g, 100.00 mmol) were added to the solution. The mixture was refluxed under N2 atmosphere for 12 h and then treated according to previous literature to obtain the compound 1 as a white solid (2.50 g). Yield: 65.6percent. 17
49.2% With copper(l) iodide; 1,10-Phenanthroline; potassium <i>tert</i>-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 24 h; Inert atmosphere Use a 50 mL two-port bottle as the reaction vessel.The reaction device is subjected to anhydrous treatment,The reflux reaction was protected by argon.Add p-iodoanisole (5.149 g, 22 mmol, 2.0 eq) to a two-necked vial.Potassium tert-butoxide (about 6 g, 60 mmol, 6.0 eq),CuI (400 mg, 2.1 mmol, 0.21 eq),1,10-phenanthroline (400 mg, 2.0 mmol, 0.2 eq), ventilated,Add xylene (25 ml) with a syringe under stirring.Add with a syringeAniline (931 mg, 0.93 mL, 10 mmol, 1.0 eq).The mixture was stirred at 130 ° C for 24 h in an oil bath.The reaction was monitored by TLC.Extract a small amount of ethyl acetate and water for 5 times with a separatory funnel.Pour the organic phase into a round bottom flask and spin dry.Add silica gel and mix.After being stirred evenly, it was separated by column chromatography (petroleum ether/ethyl acetate = 50/1: v/v).The product obtained has a mass of 1.5 g.The theoretical yield is 3.05g,The yield was 49.2percent.
32%
Stage #1: With 1,10-Phenanthroline; copper(l) chloride In o-xylene for 0.583333 h; Inert atmosphere; Schlenk technique; Reflux
Stage #2: With potassium hydroxide In o-xylene for 28 h; Inert atmosphere; Schlenk technique; Reflux
An oven dried Schlenk flask was charged with o-xylene (30 mL) and the solvent degassed. To this solution, 4-iodoanisole (15.00 g, 64.1 mmol), CuCl (0.201 g, 2.03 mmol), 1,10-phenanthroline (0.274 g, 1.5 mmol) and aniline (2.78 mL, 30.5 mmol) were added, the mixture was heated at reflux for 35 min, KOH (13.70 g, 244 mmol) was added and the mixture heated at reflux for 28 h, cooled, poured into H2O (150 mL) and extracted with CH2Cl2 (3 * 60 mL). The organic layers were combined and dried over MgSO4, filtered and the solvent removed in vacuo. The residue was suspended in hexane and purified by silica column chromatography eluting with hexane increasing to hexane:CH2Cl2 (50:50), removal of the solvent and crystallisation from hot hexane gives the title compound as a white solid. Yield 3.29 g, 32percent. 1H NMR (400 MHz, CDCl3) δ 7.16 (d, J = 7 Hz, 2H), 7.05 (d, J = 9 Hz, 4H), 6.94 (d, J = 7 Hz, 2H), 6.90-6.85 (m, 1H), 6.82 (d, J = 9 Hz, 4H), 3.80 (s, 6H). Literature: [47] 1H NMR (CDCl3): δ = 7.25-6.79 (m, 13H, Ar), 3.79 ppm (s, 6H, OCH3). ESI-MS: 305.6 [M]+.

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  • [ 87441-18-7 ]
  • [ 75581-11-2 ]
  • [ 87441-17-6 ]
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[3] Chemische Berichte, 1896, vol. 29, p. 1410
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YieldReaction ConditionsOperation in experiment
89% at 20℃; To a solution of 4-iodo-anisole (2.76 g, 11.8 mmol, 1.0 equiv.), PdCl2(PPh)2 (166 mg, 236 Mmol, 2 molpercent) and Cul (89.0 mg, 472 Mmol, 4 molpercent) in degassed NEt3 (100 mL), was added 2-ethynylbenzaldehyde (2.00 g, 15.4 mmol, 1.3 equiv.). After the reaction was stirred at room temperature over night the solvent was removed under reduced pressure. The crude material was purified by flash column chromatography (S1O2; petrolether : ethylacetate = 40:1 to 35:1 ) followed by recrystallization in ChbC /pen- tane to afford the title compound 1f as colorless solid (2.49 g, 0.5 mmol, 89percent).
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YieldReaction ConditionsOperation in experiment
78% With 1,10-Phenanthroline; copper(l) chloride; potassium hydroxide In toluene for 20 h; Inert atmosphere; Reflux To a 100 mL three-necked flask was added p-iodoanisole (1.1 g, 4.8 mmol) in this order,P-bromoaniline (0.34 g, 2.0 mmol),Potassium hydroxide (0.56 g, 10 mmol),1,10-phenanthroline (0.03 g, 0.16 mmol) and 60 mL of toluene,Fitted with a reflux condenser,Vacuum,Replace argon protection.Under argon flow,A catalytic amount of cuprous chloride was quickly added,The reaction was heated to reflux for 20 h.After TLC detection of raw materials reaction finished,The reaction was stopped,The solvent was distilled off under reduced pressure,The reaction mixture was dissolved in 100 mL of dichloromethane,And further washed three times with saturated brine (80 mL x 3)The organic phase was dried over anhydrous sodium sulfate overnight.The filtrate was collected by filtration,The solvent was removed under reduced pressure,The crude product was purified by column chromatography on silica gel (200-300 mesh [eluent,V (petroleum ether): V (ethyl acetate) = 8: 1] to give Intermediate 6 (0.60 g) as a pale yellow solid,Yield 78percent.
70.4% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In toluene at 110 - 135℃; for 12 h; Inert atmosphere A mixture of 1-iodo-4-methoxybenzene (10.00 g, 42.74 mmol), 4-bromobenzenamine (2.95 g, 17.15 mmol) and 1,10-phenanthroline anhydrous (0.62 g, 3.42 mmol) in toluene (60 mL) was heated and stirred under nitrogen atmosphere. When the temperature reached to 110 °C, the CuI (0.65 g, 3.42 mmol) and KOH (7.66 g, 136.79 mmol) were added quickly, and then the mixture was stirred at 135 °C for 12 h. After cooled to RT, the mixture was poured into distilled water (50 mL) and extracted with dichloromethane (DCM) (3 * 30 mL). The combined organic layer was dried over MgSO4 for 2 h and filtrated. The filtrate was concentrated by rotary evaporator under reduced pressure. The residue was purified by silica gel column chromatography using DCM/petroleum ether (PE) (1/5, V/V) as eluent to gain lyard powder (4.63 g, 70.4percent). 1H NMR (400 MHz, CDCl3, ppm): 7.25 (d, J = 4.0 Hz, 2H), 7.04 (d, J = 8.4 Hz, 4H), 6.83 (d, J = 8.2 Hz, 6H), 3.79 (s, 6H).
70.4% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In toluene at 110 - 135℃; for 12 h; Inert atmosphere In a 100 mL three-necked flask, 4-methoxyiodobenzene (10.0 g, 42.74 mmol) and p-bromoaniline (2.9 g,17.15 mmol), anhydrous 1,10-phenanthroline (0.6 g, 3.42 mmol) and 60 mL of toluene were added and the temperature was raised to 110 ° C under the protection of nitrogen.Copper iodide (0.7 g, 3.42 mmol) and potassium hydroxide (7.7 g, 136.79 mmol) were added rapidly and the reaction was further allowed to warm to 135 ° C and the reaction was stirred for 12 h. After cooling to room temperature, the reaction mixture was poured into 50 mL of distilled water and extracted with CH 2 Cl 2 (3 × 30 mL). The extract was washed with water, dried over anhydrous MgSO 4 and the solvent was removed under reduced pressure. The crude product was washed with CH 2 Cl 2: PE = 1: 5 V) as eluent, and separated by column chromatography to give 4.63 g of an off-white solid in a yield of 70.4percent.
62.2% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In toluene at 125℃; for 24 h; Inert atmosphere To a stirred solution of 4-iodoanisole (5.85 g, 25 mmol), 4-bromoaniline (1.72 g, 10 mmol), and 1,10-phenanthroline (0.18 g, 1 mmol) in toluene (100 mL) were added potassium hydroxide (5.61 g, 100 mmol) and copper(I) iodide (0.19 g, 1 mmol). The reaction mixture was heated under reflux for 24 h at 125 °C. The crude product was extracted into dichloromethane, and the organic layer was washed with 1 N HCl solution, brine, and water. The organic layer was dried with anhydrous MgSO4 and then the solvent was removed in vacuo. The residue was purified by column chromatography using silica gel and dichloromethane-hexane (1:1; v/v) as the eluent to give 3 (2.39 g, 62.2percent). 1H NMR (500 MHz, d6-DMSO, ppm): δ 7.31 (d, J = 9.0 Hz, 2H), 7.04-7.02 (m, 4H), 6.93-6.91 (m, 4H), 6.67 (d, J = 9.0 Hz, 2H), 3.74 (s, -OCH3 * 2, 6H). 13C NMR (126 MHz, CDCl3, ppm): δ 156.0, 147.9, 140.6, 131.7, 127.7, 126.5, 121.9, 114.8, 114.2, 112.4, 55.5. HRMS (m/z): calcd. for (C20H18BrNO2): 383.0520, found: 383.0516 [EI+]. Anal. Cald for (C20H18BrNO2): C, 62.51; H, 4.72; N, 3.65. Found: C, 62.39; H, 4.70; N, 3.52.
53.8% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In toluene at 110℃; for 48 h; Inert atmosphere Add 5.00 g of p-bromoaniline, 14.4 g of p-iodoanisole, 0.28 g of CuI, 12.8 g of KOH, and 0.26 g of 1,10-phenanthroline to a 250 mL two-necked flask. Nitrogen was three times, then 60 mL of anhydrous oxygen-free toluene was added and stirred at 110° C. for 48 hours. After the reaction is completed, it is cooled to room temperature, filtered directly, and the filter residue is washed three times with dichloromethane.The filtrate was then spin-dried under reduced pressure. The resulting crude product was subjected to column chromatography using petroleum ether and dichloromethane in a volume ratio of 3:1 as eluent to obtain 6.02 g of a yellow solid 3 with a yield of 53.8percent.

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