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[ CAS No. 111-83-1 ]

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Chemical Structure| 111-83-1
Chemical Structure| 111-83-1
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Product Details of [ 111-83-1 ]

CAS No. :111-83-1 MDL No. :MFCD00000276
Formula : C8H17Br Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :193.12 g/mol Pubchem ID :8140
Synonyms :

Safety of [ 111-83-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501 UN#:3082
Hazard Statements:H227-H315-H318-H335-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 111-83-1 ]

  • Upstream synthesis route of [ 111-83-1 ]
  • Downstream synthetic route of [ 111-83-1 ]

[ 111-83-1 ] Synthesis Path-Upstream   1~34

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YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydroxide In dimethyl sulfoxide at 90℃; for 2 h;
Stage #2: at 20 - 65℃; for 19 h;
A mixture of imidazole (1 .36 g, 20.0 mmol) and sodium hydroxide (0.80 g, 20.0 mmol) in DMSO was heated to 90 °C for 2 h, and then cooled to room temperature. A solution of 1 -bromooctane (3.46 g, 19.0 mmol) in DMSO was added dropwise to the mixture. After stirring at room temperature for 3 h, the mixture was heated up slowly to 65 °C for 16 h with constant stirring. The solution obtained was mixed with water and the product was extracted 4 times with diethyl ether. The diethyl ether phases were combined and dried with sodium sulfate. Diethyl ether was removed under vacuum and the intermediate (9) was obtained as yellow liquid (2.89 g, 89 percent). 1 H NMR (DMSO-d6): δ 7.61 (s, 2H), 7.15 (s, 1 H), 6.87 (s, 1 H), 3.93 (t, 2H), 1 .68 (m, 2H), 1 .25 (m, 10H), 0.85 (t, 3H).
87.7% With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; Inert atmosphere To a flask equipped with a stirrer, Add the thermometer to the three necked flask 0 · 440 g (11.0 mmol) of NaOH, 0.714 g (10.5 mmol) of imidazole and 10 mL of dimethylsulfoxide (DMSO) were stirred under nitrogen at 20 ° C to 25 ° C to give a clear solution. To this was added dropwise 1.93 g (10.0 mmol)Bromo octane, reaction 4 ~ 6 h, the reaction into 10 mL of water extracted with chloroform 3 X 10 mL, and then washed with water chloroform layer 4 ~ 5 times, and then dried with anhydrous MgS04, filtered to get the filtrate, Removal of chloroform yielded a pale yellow liquid, 1.58 g of N-octylimidazole, in 87.7percent yield.
85% With sodium hydroxide In tetrahydrofuran; waterReflux General procedure: A solution of imidazole 3 (30 mmol) in THF (60 mL) was treated with NaOH (25 mL, 40percent aq) and the alkyl bromide (30 mmol), and the reaction was refluxed overnight. The solvent was evaporated and the crude reaction mixture was extracted with CH2Cl2 against water. The organic layer was washed with water, dried over MgSO4 and concentrated. The final product was distilled under vacuum (~5 mbar) to provide 4 as yellow oily liquid in 80-85percent yield.
82.3%
Stage #1: With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2 h;
Stage #2: for 4 h;
General procedure: A mixture of imidazole (30 mmol, 2.04 g), potassiumhydroxide (30 mmol, 1.68 g) and dimethyl sulfoxide(10 mL) was stirred for 2 h at room temperature. Afterthat, alkyl bromide (25.0 mmol of 1-bromohexane, 1-bromooctane,1-bromodecane, 1-bromododecane, 1-bromotetradecane,1-bromohexadecane, or 1-bromooctadecane)was dropped in slowly and the mixture was stirred for anadditional 4 h. Upon completion, water (30 mL) was addedto the resulting mixture followed by extraction with chloroform(5 x 30 mL). The combined organic layer wasdried over anhydrous magnesium sulfate and the filtratewas concentrated under reduced pressure. The residue wassubjected to flash chromatography with ethyl acetate aseluent to give N-alkyl imidazole. The respective yields ofN-hexyl imidazole, N-octyl imidazole, N-decyl imidazole,N-dodecyl imidazole, N-tetradecyl imidazole, N-hexadecylimidazole and N-octadecyl imidazole are 84.6, 82.3, 81.2,80.5, 80.4, 79.8 and 79.6 percent.
60%
Stage #1: With sodium hydride In tetrahydrofuran for 0.75 h; Inert atmosphere; Cooling with ice
Stage #2: at 20℃; for 24 h; Inert atmosphere
Imidazole (3.41 g, 50 mmol) and NaH (1.34 g, 54 mmol) were dissolved in THF (10 mL) under N2 in an ice bath for 45 min, followed by addition of 1-bromooctane (9.65 g, 50 mmol). The solution was stirred for 24 h at room temperature and then concentrated under reduced pressure after filtration.The residue was purified by flash chromatography (SiO2; petroleum ether/ethyl acetate5 : 1 as eluent) to give 1 as alight yellow oil (5.97 g, 60 percent). δH (CDCl3, 400 MHz) 7.42 (1H, s), 7.01 (1H, s), 6.87 (1H, s), 3.89 (2H, t, J 8.0), 1.76–1.73 (2H, m), 1.31–1.25 (10H, m), 0.87 (3H, t, J 7.2). δC (CDCl3, 100 MHz) 136.2, 128.4, 118.1, 46.4, 31.2, 30.6, 28.6, 28.5,26.0, 22.1, 13.6. m/z (ESI) 181 ([M + H]+). m/z 181.1708. HRMS (ESI) Anal. Calc. for C11H21N2 ([M + H]+) 181.1705.

Reference: [1] Synthetic Communications, 1993, vol. 23, # 13, p. 1783 - 1786
[2] Journal of Physical Chemistry B, 2013, vol. 117, # 48, p. 15014 - 15022
[3] ChemMedChem, 2017, vol. 12, # 11, p. 835 - 840
[4] Patent: WO2018/56902, 2018, A1, . Location in patent: Page/Page column 32
[5] Patent: CN103951702, 2016, B, . Location in patent: Paragraph 0039; 0040
[6] Journal of Materials Chemistry, 2011, vol. 21, # 33, p. 12280 - 12287
[7] Carbohydrate Research, 2015, vol. 412, p. 28 - 33
[8] New Journal of Chemistry, 2007, vol. 31, # 6, p. 879 - 892
[9] Journal of Surfactants and Detergents, 2016, vol. 19, # 4, p. 681 - 691
[10] Journal of Molecular Structure, 2004, vol. 697, # 1-3, p. 131 - 135
[11] Applied Organometallic Chemistry, 2017, vol. 31, # 5,
[12] Applied Organometallic Chemistry, 2018, vol. 32, # 2,
[13] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 17, p. 2863 - 2865
[14] Inorganic Chemistry, 2017, vol. 56, # 13, p. 7558 - 7565
[15] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 825 - 829
[16] Chemistry - A European Journal, 2018, vol. 24, # 50, p. 13322 - 13335
[17] Macromolecules, 2013, vol. 46, # 12, p. 4799 - 4804
[18] Journal of Organometallic Chemistry, 2000, vol. 598, # 2, p. 409 - 416
[19] Chemistry Letters, 2005, vol. 34, # 3, p. 442 - 443
[20] Journal of Chemical and Engineering Data, 2006, vol. 51, # 4, p. 1274 - 1279
[21] Dyes and Pigments, 2013, vol. 96, # 1, p. 16 - 24,9
[22] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 423 - 427
[23] Journal of the Chinese Chemical Society, 2013, vol. 60, # 7, p. 745 - 754
[24] Chemical Biology and Drug Design, 2014, vol. 83, # 3, p. 278 - 288
[25] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 6, p. 1675 - 1680
[26] RSC Advances, 2015, vol. 5, # 4, p. 2869 - 2881
[27] RSC Advances, 2015, vol. 5, # 71, p. 57968 - 57974
[28] Journal of Molecular Catalysis A: Chemical, 2016, vol. 411, p. 34 - 39
[29] RSC Advances, 2015, vol. 5, # 28, p. 21865 - 21876
[30] Patent: US2018/255777, 2018, A1, . Location in patent: Paragraph 0047; 0048; 0065
[31] Dalton Transactions, 2018, vol. 47, # 40, p. 14241 - 14253
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Reference: [1] RSC Advances, 2015, vol. 5, # 106, p. 87200 - 87205
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  • [ 111-83-1 ]
  • [ 1068-90-2 ]
  • [ 17702-88-4 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5146 - 5151
[2] Journal of the American Chemical Society, 2000, vol. 122, # 17, p. 4032 - 4038
  • 4
  • [ 111-83-1 ]
  • [ 17702-88-4 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 41, p. 4255 - 4258
[2] Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183
  • 5
  • [ 111-83-1 ]
  • [ 6326-44-9 ]
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Reference: [1] Nagasaki med.J., 1954, vol. 29, p. 385
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  • [ 74-89-5 ]
  • [ 2439-54-5 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1704,1707
[2] J. Appl. Chem. USSR (Engl. Transl.), 1988, vol. 61, # 10, p. 2171 - 2174[3] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1988, vol. 61, # 10, p. 2365 - 2368
[4] Patent: US4572802, 1986, A,
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  • [ 74-89-5 ]
  • [ 2439-54-5 ]
  • [ 4455-26-9 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 201
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 722
[3] Journal of the American Chemical Society, 1939, vol. 61, p. 771
[4] Journal of the Chemical Society, 1947, p. 201
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  • [ 28741-08-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 15, p. 3840 - 3843
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10612 - 10615
  • 9
  • [ 121-43-7 ]
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  • [ 28741-08-4 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 28, p. 4995 - 4998
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  • [ 111-42-2 ]
  • [ 15520-05-5 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In acetonitrile for 12 h; Inert atmosphere; Reflux 1 -bromooctane (3.0 g, 1.5 mmol), diethanolamine (2.4 g, 2.3 mmol), anhydrous potassium carbonate (4.28 g, 3.1 mmol) were taken in acetonitrile (40 mL) and the contents were refluxed for 12 h nitrogen atmosphere. After cooling reaction mixture was evaporated and extracted with dichloromethane and dried over anhy. Na2S04 removed under reduced pressure to get the crude productwhich was further purified by column chromatography using dichloromethane and methanol as eluentto obtain pure 2,2'-(octylazanediyl)bis(ethan-l-ol) as colorless oil (590 mg, 91 percent).1H NMR (CDC13): δ 4.22 (brs, 2H, OHCH2), 3.86 (t, 4H, JAB = 5 Hz, -CH2OH), 3.10 (t, 4H, JAB = 4.5 Hz, -CH2N), 2.94 (t, 2H, JAB = 8 Hz, -CH2N), 1.69-1.60 (m, 2H, -CH2), 1.30-1.25 (m, 10H, - CH2), 0.87 (t, 3H, JAB = 7 Hz, -CH3).
76.7% With potassium carbonate; potassium iodide In acetonitrile for 12 h; Inert atmosphere; Reflux (1) n-octyl bromide (6.0 g, 30 mmol), diethanolamine (4.73 g, 45 mmol),Anhydrous potassium carbonate (8.29 g, 60 mmol) and potassium iodide (1.0 g) were added to a 250 mL two-necked flask, 80 mL of acetonitrile was added and the nitrogen was bubbled through for 5 minutes to replace the air in the system and then refluxed for 12 h.(2) The reaction was stopped, acetonitrile was removed by steaming, 60 mL of dichloromethane and 60 mL of water were added, and the mixture was separated. The organic phase was washed twice with water to remove excess diethanolamine. The product has a certain solubility in water, washed, the water phase and then extracted twice with methylene chloride. The organic phase was separated and dried over anhydrous sodium sulfate.(3) steamed to remove methylene chloride to obtain a light yellow liquid 5.00g, yield 76.7percent JLC detection, ethyl acetate / petroleum ether = 1: 1 as the development agent, the target product than the value of Rf = 0.33 The(4) A 250 mL single-necked flask was charged with (3) the procedure to prepare 5.00 g (23 mmol) of octyldiethanolamine, bromopropyne3.56 g (30 mmo 1) and ethanol 1 OOmL, stirred and refluxed for 12 h under stirring.(5) The excess of bromopropyne and solvent ethanol were distilled off under reduced pressure to give 7.36 g of the crude product as brownish red viscous liquid,100percent. TLC detection, dichloromethane: methanol = 6: 1, the specific value of Rf = 0.50
Reference: [1] Patent: WO2018/42367, 2018, A2, . Location in patent: Page/Page column 95; 96-97
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 185, p. 131 - 140
[3] Patent: CN106187790, 2016, A, . Location in patent: Paragraph 0044-0050
[4] Patent: US2541088, 1946, ,
[5] European Journal of Medicinal Chemistry, 1976, vol. 11, p. 115 - 124
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 13, p. 4320 - 4322
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  • [ 201230-82-2 ]
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 13, p. 4320 - 4322
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  • [ 7795-95-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 20, p. 5145 - 5149
[2] Synthesis (Germany), 2015, vol. 47, # 20, p. 3186 - 3190
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YieldReaction ConditionsOperation in experiment
95.1%
Stage #1: at 20 - 160℃; for 7 h;
Stage #2: With hydrogen bromide In water for 5 h; Reflux
2.5 ml of 1-bromooctane was charged at room temperature into a 1000 ml flask, 12.9 g of aluminum trichloride was added, Stir evenly, And then heated to 85 deg C, 1.0 mol of triethyl phosphite was added dropwise, Temperature control between 85 ~ 105 deg C, 3.0h drop finished. After the dropwise addition, Heating up to 160 ° C, Insulation for 4h to continue the reaction. After the reaction, Cooling to 80 deg C, 506.0 g of a 40percent aqueous solution of hydrogen bromide was added dropwise to the reaction system, 60min drop finished. After the dropwise addition, Heated to reflux state, Maintain 4h to react. After the reaction, The aqueous bromine solution was distilled off at 105 ° C under normal pressure, Recovering these aqueous hydrogen bromide solutions; At a vacuum of 2.5 kPa, 90 under the conditions of 1 - bromooctane distillation; Then down to room temperature, A mixed solution of n-hexane and water in a volume ratio of 6: 1 was poured into a reactor, After mixing all into the separatory funnel, Extraction liquid separation; The lower aqueous liquid recovery, The upper oil phase is transferred to the flask, The n-hexane was distilled off at atmospheric pressure at 85 ° C, Recovering these n-hexane, To give 1-octylphosphonic acid; The yield of the reaction was 95.1percent; Sampling analysis, The chromatographic purity of the product was 98.2percent.
Reference: [1] Patent: CN105153224, 2017, B, . Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0036
[2] Journal of the American Chemical Society, 1945, vol. 67, p. 1182
[3] Patent: US2397422, 1945, ,
[4] Journal of Organic Chemistry, 1960, vol. 25, p. 1000 - 1006
[5] Patent: JP5664635, 2015, B2,
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YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24 h; Take a clean two bottle, add magnet,2.44 g of p-hydroxybenzaldehyde (about 20 mmol),19.31 g of bromooctane (about 100 mmol),13.82g Potassium Carbonate and 50mlThe waterless magnetic stirring,80 °C reaction 24h.After the reaction was completed, water/methylene chloride was extracted several times and the organic phases were combined. After separation by a chromatography column, 4.68 g (approximately 99percent yield) of a pale yellow liquid was obtained.
99% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24 h; Take a clean two-neck bottle and add magnets,3.05 g of p-hydroxybenzaldehyde (about 25 mmol),24.14g of bromooctane (about 125mmol),17.25 g of potassium carbonate 20 mL of anhydrous N,N-dimethylformamide solution. The reaction was carried out at 80 ° C for 24 hours under magnetic stirring.After the end of the reaction, the water/dichloromethane was extracted several times and the organic phases were combined. Separation by chromatography gave a pale yellow liquid (yield about 99percent).
95% With potassium carbonate In acetonitrile at 80℃; for 10 h; In a 500mL round-bottomed flask were successively added p-hydroxybenzaldehyde (12.5g, 0.1mol), potassium carbonate (16.5g,0.12mol), bromo-n-octane (23.2g, 0.12mol) and 150mL of acetonitrile, magnetic stirring, and the reaction temperature is controlled at80 deg. C for 10h. After completion of the reaction the solid residue was removed by filtration using frit funnel, the solvent was removed, dissolved in dichloromethane, washed with water several of times, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation, and the residue was subjected to silica gel column chromatography, V (petroleum ether): V (ethyl acetate) = 10: 1 as eluent to give 22.2g of yellow liquid, yield 95percent.
95% With potassium carbonate In acetonitrile at 80℃; for 10 h; To a 500 mL round bottom flask was added p-hydroxybenzaldehyde (12.5 g, 0.1 mol) in that order,Potassium carbonate (16.5 g, 0.12 mol),Bromo-n-octane (23.2 g, 0.12 mol) and 150 mL of acetonitrile,Magnetic stirring,The reaction temperature was controlled at 80 ° C for 10 h.The reaction was stopped,The solid residue was removed by filtration through a suction funnel,Spin drying solvent,Diluted with methylene chloride,A lot of washing,And dried over anhydrous magnesium sulfate.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) = 10: 1]To give pale yellow liquid intermediate 1 (22.2 g)Yield 95percent.
95% With potassium carbonate In acetonitrile at 80℃; for 10 h; Into a 250mL round bottom flask added the p-hydroxy benzaldehyde (12.5 g, 0.1mol), Potassium carbonate (16.5g, 0.12mol), bromooctane (23.2 g, 0.12 mol) and acetonitrile (150mL), with magnetic stirring, the reaction temperature is controlled at 80 ° C for 10 h; stop the reaction, the solid residue is removed by suction filtration funnel, the filtrate is extracted with dichloromethane, saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate is evaporated to remove the solvent by rotary evaporation, the crude product is purified by column chromatography on silica gel (200-300 mesh) [eluent, V (petroleum ether): V (ethyl acetate) = 20: 1] and then obtained light yellow liquid intermediate 1 (22.2 g),yield 95percent.
95% With potassium carbonate In acetonitrile at 80℃; for 10 h; P-hydroxybenzaldehyde (12.5 g, 0.1 mol), potassium carbonate (16.5 g, 0.12 mol), bromo-n-octane (23.2 g, 0.12 mol) and acetonitrile (150 ml) were added successively to a 250 ml round bottom flask. The reaction was carried out at 80 ° C for 10 h with magnetic stirring. The reaction was stopped and the solid residue was removed by suction filtration through a suction funnel. The filtrate was extracted with dichloromethane, washed with saturated brine and dried over anhydrous magnesium sulfate. The filtrate was evaporated to remove the solvent by rotary evaporation. The crude product was purified by silica gel (200-300 mesh) column chromatography [eluent, V (petroleum ether): V (ethyl acetate) = 20: 1] to give a pale yellow liquid intermediate 1 (22.2 g), 95percent
95% With potassium carbonate In acetonitrile at 80℃; for 10 h; In the 500 ml round-bottom flask was added p-hydroxybenzaldehyde (12.5g, 0.1mol), potassium carbonate (16.5g, 0.12mol), bromo-n-octane (23.2g, 0 . 12mol) and acetonitrile (150 ml), the reaction temperature is controlled at 80 °C magnetic stirring reaction 10h. After the reaction is ended funnel filtration to remove the solid residue of the sand core, the filtrate is extracted with ethyl acetate, saturated salt water washing, drying with anhydrous magnesium sulfate, get the crude product. The crude product using silica gel (200-300 mesh) column chromatography [eluant, V (petroleum ether): V (ethyl acetate) =10:1] yellow liquid intermediates purified to get 1,22.2g, yield 95percent.
91% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 9 h; General procedure: 4-Hydroxybenzaldehyde (12.5 g, 0.1 mol), potassium carbonate (16.5 g, 0.12 mol) and dimethylformamide (300 mL) were placed in a three-necked 1 L round bottomed flask. The reaction mixture was heated to 80 °C and stirred. To the warm solution the appropriate alkylbromide (19.8 g for 1-bromohexane; 23.2 g for 1-bromooctane; 26.5 g for 1-bromodecane; 29.9 g for 1-bromododecane; 0.12 mol) was added dropwise over 1 h. The mixture was then heated at 80 °C for 8 h. After cooling down to room temperature the mixture was diluted with water (300 mL). The aqueous phase was extracted with dichloromethane (3.x.300 mL). The combined organic layer was washed twice with aq NaOH (10percentmol), water and dried with MgSO4. After evaporation of solvent on a rotary evaporator the corresponding products were obtained as pale yellow oils, which were subsequently used without purification.
86%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.166667 h; Inert atmosphere
Stage #2: at 25℃; Inert atmosphere
Procedure: Potassium carbonate (340 mg, 2.46 mmol, 1.5 eq.) and 4-hydroxybenzaldehyde(compound S5, 200 mg, 1.64 mmol, 1 eq.) were added to an oven-dried round-bottomed flask.This flask was evacuated using three nitrogen-vacuum purge cycles. Dry DMF (50 mL) was addedvia syringe and the reaction mixture stirred for 10 minutes at room temperature. 1-bromooctane(compound S6, 348 mg, 0.311 mL, 1.80 mmol, 1.1 eq.) was added via syringe and the reactionmixture stirred at room temperature for 14 hours under an inert nitrogen atmosphere. The reactionmixture was then diluted with water (100 mL) and extracted with diethyl ether three times (40 mLeach). The combined organic layer was dried over sodium sulfate, filtered, and concentrated ona rotary evaporator. The crude product was purified on a silica plug (eluent: 10percent ethyl acetate inn-hexanes) giving a yellow solid in 86percent yield (332 mg).
80%
Stage #1: With potassium carbonate In acetone at 20℃; for 0.0833333 h;
Stage #2: With potassium iodide In acetone for 6 h; Reflux
4-Hydroxybenzaldehyde (0.61 g, 5 mmol) was dissolved in acetone.
Potassium carbonate (0.759 g, 5.5 mmol) was added and the resulting mixture was stirred for 5 minutes at room temperature.
To the mixture, 1-bromooctane (0.965 g, 5 mmol) and potassium iodide (0.83 g, 5 mmol) were added, followed by refluxing for 6 h. TLC showed the completion of the reaction.
Solvent was removed in vacuo and the resulting residue was extracted with ethyl acetate (2 * 10 mL), treated with brine, and dried over sodium sulfate.
Flash chromatography using 5percent ethyl acetate in hexane afforded a gummy colorless compound (0.94 g, 80percent).
1H NMR (600 MHz, CDCl3, δ): 9.88 (s, 1H), 7.83 (d, J = 8.7 Hz, 2H), 6.99 (d, J = 8.7 Hz, 2H), 4.04 (t, J = 6.5 Hz, 2H), 1.81 (quin., J1 = 6.6 Hz, J2 = 7.2 Hz, 2H), 1.46 (quin., J1 = 6.8 Hz, J2 = 7.6 Hz, 2H), 1.32 (m, 8H), 0.89 (t, J = 6.8 Hz, 3H).
77% With potassium hydroxide In ethanol for 96 h; Reflux General procedure: These compounds were prepared according to the Williamson synthesis of ethers by a known method [22-24]. 4-hydroxybenzaldehyde (8.72 g, 71.5 mmol) was added to a solution of potassium hydroxide (4 g) in ethanol (60 mL). The mixture was treated with n-alkyl halide(71.5 mmol) (methyl iodide was used in the preparation of A1, while n-alkylbromide used inthe preparation of A1-A13) and heated under reflux. The reaction was monitored by thin-layerchromatography (TLC) using chloroform as eluent, and the optimal time of each reaction was determined. The ethanol was evaporated and the residue was dissolved in diethyl ether. The ethereal was washed with an aqueous solution of potassium hydroxide (10percent) followed by water until a pH = 7 was obtained. The organic layer was dried over sodium sulfate anhydrous and evaporated to give the desired product. The details of the reaction conditions for the preparation of each compound are described in Table 1.
72%
Stage #1: With potassium hydroxide In acetonitrile at 20℃; for 1 h;
Stage #2: for 4 h; Reflux
General procedure: To 80 mL CH3CN and 4-hydroxybenzaldehyde (42 mmol) wasadded potassium hydroxide (46 mmol). The solution was stirred at room temperature for 1h and then the bromoalkanes (46 mmol) corresponding were added. The reactionmixture was refluxed for 4 h and the precipitate was filtered off. The filtrate wasevaporated in vacuum and purified by distillation under a reduced pressure. All the aldehydes were obtained as pale yellow viscous liquids.
66%
Stage #1: With sodium ethanolate In ethanol at 70℃; for 0.333333 h;
Stage #2: at 70℃; for 48 h;
General procedure: 4-Hydroxybenzaldehyde (244 mg, 2 mmol) was added to a solution of 46 mg (2 mmol) of sodium ethoxide in 12 mL of ethanol and stirred until completely consumed. Solution was kept under reflux (70 °C) with magnetic stirring for 20 min. The corresponding alkylation agent (n-alkyl bromide, 2 mmol) was added to the system and the temperature was maintained at 70 °C with stirring for 48 h. Compounds 2a-d were isolated by solvent extraction (ethyl acetate/water, 3:1) and then purified by distillation. Compound 2e was fussily purified by flash chromatography in silica gel (hexane/ethyl acetate; 95:05, Rf 0.4).Compound 2a (73percent yield); IR (NaCl, cm-1): ν 2985, 2935, 2738, 1692, 1260, 1163, 1040, 836; 1H NMR (250 MHz, CDCl3, TMS) δ (ppm): 9.87 (s, 1H), 7.82 (d, 2H, J = 8.9 Hz), 6.98 (d, 2H, J = 8.6 Hz), 4.12 (q, 2H, J = 7.0 Hz), 1.45 (t, 3H, J = 7.0 Hz); EI-MS, m/z 150 [M]+, 121 [HO-C6H4-CO]+, 93 [HO-C6H4]+. Compound 2b (75percent yield); IR (NaCl, cm-1): ν 2967, 2876, 2734, 1692, 1602, 1261, 1160, 834; 1H NMR (250 MHz, CDCl3, TMS) δ (ppm): 9.88 (s, 1H), 7.82 (d, 2H, J = 8.8 Hz), 6.99 (d, 2H, J = 8.8 Hz), 4.00 (t, 2H, J = 6.5 Hz), 1.85 (h, 2H, J = 7.3 Hz), 1.05 (t, 3H, J = 7.5 Hz);EI-MS, m/z 164 [M]+, 121 [HO-C6H4-CO]+, 93 [HO-C6H4]+. Compound 2c (73percent yield); IR (NaCl, cm-1): ν 2964, 2872, 2733, 1692, 1600, 1260, 1158, 828; 1H NMR (250 MHz, CDCl3, TMS) δ (ppm): 9.87 (s, 1H), 7.82 (d, 2H, J = 8.8 Hz), 6.99 (d, 2H, J = 8.7 Hz), 4.04 (t, 2H, J = 6.5 Hz), 1.80 (p, 2H, J = 6.9 Hz), 1.50 (h, 2H, J = 7.5 Hz), 0.99 (t, 3H, J = 7.3 Hz); EI-HRMS, calculated for C11H14O2m/z 178.0994, found: m/z 178.0898 [M]+, 121.0211 [HO-C6H4-CO]+ (calcd 121.0290), 93.0286 [HO-C6H4]+ (calcd 93.0340). Compound 2d (66percent yield); IR (NaCl, cm-1): ν 2931, 2856, 2741, 1697, 1600, 1254, 1156, 832; 1H NMR (250 MHz, CDCl3, TMS) δ (ppm): 9.87 (s, 1H), 7.83 (d, 2H, J = 8.8 Hz), 6.99 (d, 2H, J = 8.7 Hz), 4.03 (t, 2H, J = 6.5 Hz), 1.81 (p, 2H), 1.29-152 (m, 10H), 0.89 (t, 3H, J = 6.6 Hz); EI-MS, m/z 234 [M]+, 121 [HO-C6H4-CO]+, 93 [HO-C6H4]+. Compound 2e (isolated as a white solid, mp 44 °C, in 73percent yield); IR (KBr, cm-1): ν 2913, 2852, 2730, 1691, 1603, 1255, 1174, 837; 1H NMR (250 MHz, CDCl3, TMS) δ (ppm): 9.88 (s, 1H), 7.82 (d, 2H, J = 8.8 Hz), 6.99 (d, 2H, J = 8.8 Hz), 4.03 (t, 2H, J = 6.5 Hz), 1.81 (p, 2H, J = 6.7 Hz), 1.26-1.49 (m, 26H), 0.88 (t, 3H, J = 6.9 Hz); EI-HRMS, calculated for C23H38O2m/z 346.2872, found: m/z 346.2749 [M]+, 121.0077 [HO-C6H4-CO]+ (calcd 121.0290).
6.25 g With sodium carbonate In ethanolReflux 4 g (33 mmoL) of p-hydroxybenzaldehyde was weighed out of a 250 mL round bottom flask,Dissolved in 50 mL of ethanol,And then added to it8 g of Na2CO3 was stirred. After 5 min, 7.6 g (39 mmol) of bromooctane was added and the mixture was refluxed overnight. The reaction solution was washed with saturated brine and dried over anhydrous sodium sulfate.After filtration, the solvent was removed by distillation under reduced pressure to give 6.25 g of a colorless oily liquid as an intermediate;

Reference: [1] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 3, p. 562 - 571
[2] Patent: CN108102408, 2018, A, . Location in patent: Paragraph 0036-0039
[3] Patent: CN108503658, 2018, A, . Location in patent: Paragraph 0032; 0033; 0036; 0037
[4] European Journal of Organic Chemistry, 2006, # 19, p. 4379 - 4384
[5] European Journal of Organic Chemistry, 2004, # 18, p. 3865 - 3871
[6] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1027 - 1035
[7] European Journal of Medicinal Chemistry, 1993, vol. 28, # 1, p. 3 - 12
[8] Patent: CN105732680, 2016, A, . Location in patent: Paragraph 0022
[9] Patent: CN106221280, 2016, A, . Location in patent: Paragraph 0058; 0059
[10] Patent: CN106632438, 2017, A, . Location in patent: Paragraph 0059; 0060
[11] Patent: CN106905354, 2017, A, . Location in patent: Paragraph 0068; 0069
[12] Patent: CN106008582, 2016, A, . Location in patent: Paragraph 0048; 0049
[13] Canadian Journal of Chemistry, 2010, vol. 88, # 7, p. 639 - 645
[14] Chemical Communications, 2017, vol. 53, # 37, p. 5103 - 5106
[15] Tetrahedron, 2012, vol. 68, # 39, p. 8172 - 8180
[16] Journal of the Chemical Society, Dalton Transactions, 2000, # 9, p. 1437 - 1445
[17] Journal of Materials Chemistry C, 2017, vol. 5, # 21, p. 5199 - 5206
[18] Journal of Physical Chemistry B, 2015, vol. 119, # 12, p. 4539 - 4551
[19] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 17 - 21
[20] Synlett, 2018, vol. 29, # 19, p. 2515 - 2522
[21] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 154, p. 267 - 276
[22] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 154, p. 277 - 288
[23] New Journal of Chemistry, 2014, vol. 38, # 9, p. 4235 - 4248
[24] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2011 - 2027
[25] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 160 - 178
[26] Luminescence, 2016, vol. 31, # 8, p. 1448 - 1455
[27] New Journal of Chemistry, 2016, vol. 40, # 1, p. 393 - 401
[28] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 8, p. 1676 - 1680
[29] Molecular Crystals and Liquid Crystals, 2017, vol. 648, # 1, p. 114 - 129
[30] Australian Journal of Chemistry, 2012, vol. 65, # 10, p. 1426 - 1435,10
[31] European Journal of Organic Chemistry, 2009, # 6, p. 889 - 897
[32] Tetrahedron Letters, 2011, vol. 52, # 49, p. 6569 - 6572
[33] Physical Chemistry Chemical Physics, 2016, vol. 18, # 22, p. 15025 - 15038
[34] Chemical Communications, 2005, # 23, p. 2921 - 2923
[35] New Journal of Chemistry, 2011, vol. 35, # 6, p. 1194 - 1197
[36] Carbohydrate Research, 2012, vol. 353, p. 69 - 78
[37] Synthetic Communications, 2001, vol. 31, # 1, p. 1 - 7
[38] Journal of Materials Chemistry, 2004, vol. 14, # 7, p. 1117 - 1127
[39] Journal of Organic Chemistry, 2001, vol. 66, # 9, p. 2966 - 2977
[40] Acta Chimica Academiae Scientiarum Hungaricae, 1954, vol. 4, p. 303,307
[41] Journal of the Chemical Society, Chemical Communications, 1992, # 5, p. 410 - 411
[42] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 241, p. 69 - 76
[43] Journal of Materials Chemistry, 1996, vol. 6, # 3, p. 357 - 363
[44] Canadian Journal of Chemistry, 1997, vol. 75, # 3, p. 318 - 325
[45] Journal of Materials Chemistry, 1997, vol. 7, # 3, p. 429 - 433
[46] Journal of the Indian Chemical Society, 1996, vol. 73, # 10, p. 507 - 511
[47] Journal of Organometallic Chemistry, 1998, vol. 551, # 1-2, p. 271 - 280
[48] Molecular Crystals and Liquid Crystals, 2003, vol. 393, p. 41 - 48
[49] Molecular Crystals and Liquid Crystals, 2006, vol. 451, # 1, p. 127 - 138
[50] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2635 - 2640
[51] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 350, p. 151 - 159
[52] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 55 - 71
[53] Patent: US5965743, 1999, A,
[54] Patent: US5464865, 1995, A,
[55] Patent: US5618787, 1997, A,
[56] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 6, p. 1020 - 1024
[57] Chemistry and Physics of Lipids, 2008, vol. 155, # 2, p. 98 - 113
[58] Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 5, p. 752 - 754
[59] Molecular Crystals and Liquid Crystals, 2010, vol. 528, p. 120 - 137
[60] Molecular Crystals and Liquid Crystals, 2012, vol. 562, p. 98 - 113
[61] Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 274 - 282
[62] Tetrahedron, 2011, vol. 67, # 42, p. 8120 - 8130
[63] Molecules, 2011, vol. 16, # 9, p. 7789 - 7802
[64] Molecular Crystals and Liquid Crystals, 2011, vol. 542, p. 84 - 98
[65] Chinese Chemical Letters, 2012, vol. 23, # 7, p. 769 - 772
[66] Patent: US2012/214858, 2012, A1, . Location in patent: Page/Page column 28-29
[67] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 88, p. 10895 - 10897,3
[68] Patent: US2013/101544, 2013, A1, . Location in patent: Page/Page column
[69] Canadian Journal of Chemistry, 2013, vol. 91, # 3, p. 196 - 205
[70] Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 64 - 76
[71] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 106 - 115
[72] Molecular Crystals and Liquid Crystals, 2014, vol. 592, # 1, p. 44 - 62
[73] RSC Advances, 2014, vol. 4, # 49, p. 25940 - 25947
[74] Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 13 - 22
[75] RSC Advances, 2014, vol. 4, # 109, p. 64371 - 64378
[76] RSC Advances, 2015, vol. 5, # 55, p. 44274 - 44281
[77] Letters in Drug Design and Discovery, 2015, vol. 12, # 5, p. 430 - 438
[78] Patent: US9126890, 2015, B2,
[79] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 152, p. 318 - 326
[80] Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 46 - 54
[81] Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 11 - 19
[82] Molecular Crystals and Liquid Crystals, 2016, vol. 633, # 1, p. 54 - 62
[83] Molecular Crystals and Liquid Crystals, 2016, vol. 633, # 1, p. 80 - 90
[84] Molecular Crystals and Liquid Crystals, 2016, vol. 634, # 1, p. 50 - 57
[85] Molecular Crystals and Liquid Crystals, 2016, vol. 637, # 1, p. 19 - 27
[86] Molecular Crystals and Liquid Crystals, 2016, vol. 638, # 1, p. 27 - 34
[87] Molecular Crystals and Liquid Crystals, 2016, vol. 638, # 1, p. 35 - 43
[88] Molecular Crystals and Liquid Crystals, 2016, vol. 638, # 1, p. 68 - 76
[89] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 1 - 12
[90] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 13 - 27
[91] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 40 - 51
[92] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 52 - 61
[93] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 129 - 140
[94] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 159 - 167
[95] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 178 - 187
[96] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 216 - 232
[97] Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 241 - 251
[98] Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 10 - 22
[99] Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 30 - 37
[100] Dyes and Pigments, 2016, vol. 128, p. 131 - 140
[101] Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 154 - 161
[102] Journal of Chemical Sciences, 2016, vol. 128, # 7, p. 1033 - 1036
[103] Dyes and Pigments, 2017, vol. 137, p. 75 - 83
[104] Patent: US2016/340299, 2016, A1, . Location in patent: Paragraph 0039; 0040
[105] Patent: CN103641742, 2016, B, . Location in patent: Paragraph 0036-0039
[106] Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 99 - 110
[107] Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 143 - 157
[108] Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 84 - 98
[109] Molecular Crystals and Liquid Crystals, 2017, vol. 648, # 1, p. 53 - 65
[110] Organic Electronics: physics, materials, applications, 2017, vol. 49, p. 321 - 333
[111] Patent: US2017/355908, 2017, A1, . Location in patent: Paragraph 0064
[112] Chemistry - An Asian Journal, 2018, vol. 13, # 8, p. 1012 - 1023
  • 16
  • [ 111-83-1 ]
  • [ 88-99-3 ]
  • [ 117-84-0 ]
Reference: [1] Patent: US3959347, 1976, A,
  • 17
  • [ 111-83-1 ]
  • [ 88-99-3 ]
  • [ 117-84-0 ]
Reference: [1] Synthesis, 1985, # 1, p. 40 - 45
  • 18
  • [ 111-83-1 ]
  • [ 106-37-6 ]
  • [ 51554-93-9 ]
Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 20, p. 4622 - 4632
  • 19
  • [ 111-83-1 ]
  • [ 19812-93-2 ]
  • [ 52364-73-5 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 48 h; General procedure: 4'-Hydroxybiphenyl-4-carbonitrile (1) (20.0 g, 0.1 mol), potassium carbonate (28.0 g, 0.2 mol) and DMF (600 mL) were placed in a 1000 mL flask and stirred. The corresponding alkylbromide (20.0 g for 1-bromohexane, 23.0 g for 1-bromo-octane, 0.12 mol) was added and the reaction mixture was heated at 120 °C for 48 h. The mixture was then cooled to room temperature and poured onto ice water (1000 mL) and left to stand overnight. The precipitated product was isolated by filtration and crystallized from ethanol.
Reference: [1] Molecular Crystals and Liquid Crystals, 2008, vol. 480, # 1, p. 287 - 294
[2] Tetrahedron, 2012, vol. 68, # 39, p. 8172 - 8180
[3] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 268, p. 21 - 44
[4] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[5] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
[6] Journal of the Brazilian Chemical Society, 2014, vol. 25, # 8, p. 1493 - 1503
  • 20
  • [ 111-83-1 ]
  • [ 5324-84-5 ]
Reference: [1] Journal of the American Chemical Society, 1935, vol. 57, p. 571
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 20, p. 5145 - 5149
  • 21
  • [ 111-83-1 ]
  • [ 75844-69-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 37, p. 11947 - 11951[2] Angew. Chem., 2018, vol. 130, p. 12123 - 12127,5
  • 22
  • [ 111-83-1 ]
  • [ 121554-09-4 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 365, p. 171 - 179
[2] Chemistry - An Asian Journal, 2014, vol. 9, # 1, p. 104 - 109
  • 23
  • [ 872-31-1 ]
  • [ 111-83-1 ]
  • [ 65016-62-8 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With magnesium In diethyl ether for 2 h; Inert atmosphere
Stage #2: for 24 h; Cooling with ice
Compound 9 was synthesized from the reported process (Chochos CL, Economopoulos SP, Deimede V, Gregoriou VG, Lloyd MT, Malliaras GG, Kallitsis JK, et al. Synthesis of a soluble n-type cyano substituted polythiophene derivative: solar cells. J Phys Chem C 2007; 111: 10732-40).1-Bromooctane (28.7 mL)Was added dropwise to a solution of magnesium (4.63 g, 193 mmol) in anhydrous diethyl ether (130 mL). The mixture,And stirred in a nitrogen atmosphere for 2 h.The final Grignard reagent was added dropwise to a flask containing 3-bromothiophene (19 g, 116.6 mmol) and Ni (dppp) Cl2 (0.31 g, 0.571 mmol). After stirring and heating for 24 h,Contained in an ice bath,HCl (2N) was extracted with diethyl ether.The organic layer was dehydrated with sodium sulfate,Concentrated by evaporation under reduced pressure and purified by column chromatography with hexane to give a colorless oil (15.54 g, 68percent).
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 13, p. 3894 - 3901
[2] Structural Chemistry, 2012, vol. 23, # 6, p. 1751 - 1760
[3] Patent: KR2018/17709, 2018, A, . Location in patent: Paragraph 0196; 0199; 0200-0202
[4] Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381
[5] RSC Advances, 2016, vol. 6, # 82, p. 78984 - 78993
  • 24
  • [ 3141-26-2 ]
  • [ 111-83-1 ]
  • [ 65016-62-8 ]
  • [ 161746-06-1 ]
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 34, p. 10735 - 10744
  • 25
  • [ 111-83-1 ]
  • [ 145543-83-5 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 82, p. 78984 - 78993
  • 26
  • [ 1134-35-6 ]
  • [ 111-83-1 ]
  • [ 142646-58-0 ]
YieldReaction ConditionsOperation in experiment
45% With n-butyllithium; diisopropylamine In tetrahydrofuran at 0 - 20℃; for 15 h; Inert atmosphere Diisopropylamine (28.0 mL, 0.160 mol, 2.66 equiv.) was dissolved in dry THF (60 mL) under an argon atmosphere. n-butylithium (107.0 mL, 0.160 mol, 2.66 equiv.) was added dropwise at 0 °C and the solution was stirred for 1 h. Afterwards, a solution of 4,4′-dimethyl-2,2′-bipyridine (11.0 g, 0.060 mol, 1 eq.) in dry THF (300 mL) was slowly added and the orange solution was stirred for 3 h. The reaction mixture was kept at 0 °C and bromooctane (28.0 mL, 0.160 mol, 2.66 equiv.) in dry THF (20 mL) was added. The reaction mixture was then allowed to warm to room temperature. After stirring for 12 h the reaction was quenched first with water (20 mL), then poured into an ice/ water mixture and extracted with diethylether. The resulting yellow oil was recrystallized from hexane, redissolved in DCM, extracted with diluted NaOH, dried over MgSO4, filtered and the solvent removed in vacuo. Drying in high vacuum yielded the desired product (11.02 g, 0.027 mol, 45 percent). 1H NMR (500 MHz, DMSO) δ in ppm= 8.85 (s, 1H), 8.83 (s, 1H), 7.28 (s, 1H), 7.27 (s, 1H), 2.68 (t, J= 7.6 Hz, 4H), 1.62 (p, J= 8.2, 6.9 Hz, 4H), 1.32–1.11 (m, 24H), 0.83 (t, J= 6.5 Hz, 6H). HRMS (ESI) m/z: [M+H]+ calcd. for (C28H44) 409.358; found 409.3581.
Reference: [1] Dyes and Pigments, 2014, vol. 104, p. 24 - 33
[2] Journal of the American Chemical Society, 1998, vol. 120, # 2, p. 305 - 316
  • 27
  • [ 111-83-1 ]
  • [ 302554-81-0 ]
Reference: [1] Journal of Materials Chemistry, 2011, vol. 21, # 34, p. 12969 - 12976
[2] Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14031 - 14046
[3] RSC Advances, 2014, vol. 4, # 91, p. 50027 - 50034
  • 28
  • [ 111-83-1 ]
  • [ 196207-58-6 ]
Reference: [1] Macromolecules, 2004, vol. 37, # 11, p. 4087 - 4098
[2] Journal of Materials Chemistry, 2012, vol. 22, # 15, p. 7515 - 7528
[3] Tetrahedron Letters, 2015, vol. 56, # 52, p. 7145 - 7149
[4] Patent: CN106187908, 2016, A,
[5] Patent: CN106946878, 2017, A,
[6] Patent: CN107011269, 2017, A,
[7] Patent: CN107879968, 2018, A,
[8] Patent: CN108530387, 2018, A,
  • 29
  • [ 111-83-1 ]
  • [ 16433-88-8 ]
  • [ 196207-58-6 ]
Reference: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 17, p. 3874 - 3881
  • 30
  • [ 111-83-1 ]
  • [ 406726-92-9 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5705 - 5711
[2] Patent: CN107266354, 2017, A,
[3] Patent: CN107445885, 2017, A,
  • 31
  • [ 6007-82-5 ]
  • [ 111-83-1 ]
  • [ 773881-43-9 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 5, p. 996 - 999
  • 32
  • [ 111-83-1 ]
  • [ 1362606-94-7 ]
  • [ 566939-58-0 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 5, p. 996 - 999
  • 33
  • [ 111-83-1 ]
  • [ 955964-73-5 ]
Reference: [1] Polymer, 2017, vol. 119, p. 274 - 284
  • 34
  • [ 111-83-1 ]
  • [ 128-59-6 ]
  • [ 85652-50-2 ]
YieldReaction ConditionsOperation in experiment
72% With 18-crown-6 ether; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 8 h; Taking 1.21g (2.48mmol) 16, 17-dihydroxy Anthracyclinone purple puts in 100 ml flask, add 50mLN-methyl pyrrolidone, heating 10 min to 100 °C the 16, 17-dihydroxy Anthracyclinone purple disperse as much as possible. Then add 1.00g (7.2mmol) no water K2CO3, 0.98g (5.08mmol) 1-polybromide octane, and presence of 18-crown -6. Maintain reaction temperature 100 °C, reaction 8 hours the reaction is stopped.The reaction solution is poured into 100 ml water, fully mixing, filtering, drying to obtain the crude product. Dichloromethane is used for dissolving the crude product, filtering to remove undissolved components. turns on lathe does dichloromethane, to obtain the solid, dried to obtain 1.26g grams of product, yield is 72percent. The silica gel chromatographic column, to CH2Cl2: CH3OH=20 1 as eluant, further elution separation and purification.
Reference: [1] Patent: CN103804163, 2016, B, . Location in patent: Paragraph 0036; 0037; 0038
[2] Frontiers of Chemistry in China, 2010, vol. 5, # 2, p. 200 - 207
[3] Dyes and Pigments, 2012, vol. 95, # 2, p. 377 - 383
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