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Chemical Structure| 39630-68-7
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Product Details of [ 39630-68-7 ]

CAS No. :39630-68-7 MDL No. :MFCD00183535
Formula : C12H14O5 Boiling Point : -
Linear Structure Formula :- InChI Key :PUZBTHGPBGQFLW-UHFFFAOYSA-N
M.W : 238.24 Pubchem ID :606456
Synonyms :

Safety of [ 39630-68-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 39630-68-7 ]

* 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.

  • Downstream synthetic route of [ 39630-68-7 ]

[ 39630-68-7 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 64-17-5 ]
  • [ 618-83-7 ]
  • [ 39630-68-7 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid for 48h; Reflux; 2 2.2. 10Et A solution of 5-hydroxyisophthalic acid (6.17 g, 33.8 mmol) and p-toluenesulfonic acid monohydrate (2.38 g, 14 mmol) in ethanol (800 mL) was refluxed for 2 days. After the removal of the solvent in vacuo, the residue was dissolved in ethyl acetate, washed with sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated to give 10Et (7.92 g, 100%) as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 10.29 (s, 1H), 7.95-7.93 (m, 1H), 7.57 (d, J = 1.4 Hz, 2H), 4.32 (q, J = 7.1 Hz, 4H), 1.32 (t, J = 7.1 Hz, 6H) ppm.
98% With acetyl chloride for 4h; Heating;
96% With sulfuric acid Heating;
95% With hydrogenchloride for 2h;
95.65% With sulfuric acid for 48h; Heating;
95% With hydrogenchloride for 36h; Heating;
95% With sulfuric acid Heating;
95% With sulfuric acid Heating;
92% With sulfuric acid Heating;
89% With sulfuric acid Reflux; 1 A catalytic amount of concentrated sulfuric acid (1.0 mL) was added dropwise to a solution of Compound 1 (18.2 g, 0.1 mol) in ethanol (100 mL) at room temperature and then stirred at reflux overnight.Cooled to room temperature and evaporated to dryness under reduced pressure to give 21.2 g of compound 2 in 89% yield.
86% With sulfuric acid for 120h; Heating;
84% With sulfuric acid for 36h; Reflux; 1.3 Step 3: Preparation of diethyl 5-hydroxyisophthalate (V) 5-hydroxyisophthalic acid (IV) (10 g, 55 mmol) was added to a 500 mL round bottom flask equipped with a reflux condenser and a magnetic stirrer, and anhydrous ethanol (150 mL) was added to complete dissolution. Then, concentrated sulfuric acid (5 mL) was added dropwise to the flask, and the reaction solution was refluxed for 36 h. The TLC reaction was complete. The reaction solution was cooled to room temperature, and the ethanol was distilled off under reduced pressure. Then, 5% sodium bicarbonate solution (100 mL) and ethyl acetate (3 x 100 mL) were added and the organic phase was washed with saturated brine (2 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to give 10.9 g of a white solid in 84% yield. The resulting product was directly reacted with the next step.
With hydrogenchloride
With sulfuric acid Heating;
With sulfuric acid for 24h; Reflux;

Reference: [1]Oguri, Takahiro; Kawahara, Akie; Kihara, Nobuhiro [Polymer, 2016, vol. 99, p. 83 - 89]
[2]Zhang, San-Qi; Fukase, Koichi; Izumi, Minoru; Fukase, Yoshiyuki; Kusumoto, Shoichi [Synlett, 2001, # 5, p. 590 - 596]
[3]Lakshmi; Hanshaw, Roger G.; Smith, Bradley D. [Tetrahedron, 2004, vol. 60, # 49, p. 11307 - 11315]
[4]Collman, James P.; Brauman, John I.; Fitzgerald, Jeffrey P.; Hampton, Philip D.; Naruta, Yoshinori; et al. [Journal of the American Chemical Society, 1988, vol. 110, # 11, p. 3477 - 3486]
[5]Motesharei, Kianoush; Myles, David C. [Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7328 - 7336]
[6]Hu, Kejiang; Bradshaw, Jerald S.; Dalley, N.Kent; Krakowiak, Krzysztof E.; Wu, Naijun; Lee,Milton L. [Journal of Heterocyclic Chemistry, 1999, vol. 36, # 2, p. 381 - 388]
[7]Lin, Wenwei; Baron, Oliver; Knochel, Paul [Organic Letters, 2006, vol. 8, # 24, p. 5673 - 5676]
[8]Del Amo, Vicente; Dubbaka, Srinivas Ready; Krasovskiy, Arkady; Knochel, Paul [Angewandte Chemie - International Edition, 2006, vol. 45, # 46, p. 7838 - 7842]
[9]Dias, Felix B.; Batty, Simon V.; Ungar, Goran; Voss, Jonathan P.; Wright, Peter V. [Journal of the Chemical Society - Faraday Transactions, 1996, vol. 92, # 14, p. 2599 - 2606]
[10]Current Patent Assignee: XIAMEN UNIVERSITY - CN106913884, 2017, A Location in patent: Paragraph 0029; 0030; 0031
[11]Ashton, Peter R.; Anderson, Derek W.; Brown, Christopher L.; Shipway, Andrew N.; Stoddart, J. Fraser; Tolley, Malcolm S. [Chemistry - A European Journal, 1998, vol. 4, # 5, p. 781 - 795]
[12]Current Patent Assignee: NORTHEAST NORMAL UNIVERSITY - CN106831397, 2017, A Location in patent: Paragraph 0006; 0010
[13]Heine [Chemische Berichte, 1880, vol. 13, p. 493]
[14]Motesharei, Kianoush; Myles, David C. [Journal of the American Chemical Society, 1994, vol. 116, # 16, p. 7413 - 7414]
[15]Zamora-Olivares, Diana; Kaoud, Tamer S.; Dalby, Kevin N.; Anslyn, Eric V. [Journal of the American Chemical Society, 2013, vol. 135, # 39, p. 14814 - 14820]
  • 2
  • [ 39630-68-7 ]
  • [ 106-93-4 ]
  • [ 113597-99-2 ]
YieldReaction ConditionsOperation in experiment
53% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;
  • 3
  • [ 39630-68-7 ]
  • [ 106-93-4 ]
  • [ 113585-29-8 ]
YieldReaction ConditionsOperation in experiment
64% With potassium carbonate In acetone at 60℃; for 24h;
57% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;
  • 4
  • [ 39630-68-7 ]
  • [ 106-95-6 ]
  • [ 88194-15-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; sodium 1.) ethanol, 3 h; Multistep reaction;
  • 5
  • [ 39630-68-7 ]
  • [ 109-64-8 ]
  • [ 135989-89-8 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In N,N-dimethyl-formamide for 60h; Ambient temperature;
  • 6
  • [ 39630-68-7 ]
  • [ 91-13-4 ]
  • [ 155186-12-2 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In N,N-dimethyl-formamide
80% With potassium carbonate In N,N-dimethyl-formamide for 60h; Ambient temperature;
80% With potassium carbonate In N,N-dimethyl-formamide at 20℃;
  • 7
  • [ 39630-68-7 ]
  • [ 626-15-3 ]
  • [ 147566-72-1 ]
YieldReaction ConditionsOperation in experiment
89.5% With potassium carbonate In N,N-dimethyl-formamide
80% With potassium carbonate In N,N-dimethyl-formamide at 20℃;
  • 8
  • [ 39630-68-7 ]
  • [ 156750-11-7 ]
  • [ 156750-07-1 ]
YieldReaction ConditionsOperation in experiment
96.5% With potassium carbonate In N,N-dimethyl-formamide for 12h; Ambient temperature;
  • 9
  • [ 31643-49-9 ]
  • [ 39630-68-7 ]
  • 5-(3,4-Dicyano-phenoxy)-isophthalic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;
  • 10
  • [ 16695-22-0 ]
  • [ 39630-68-7 ]
  • [ 208511-31-3 ]
  • 11
  • [ 39630-68-7 ]
  • [ 100-39-0 ]
  • [ 251912-45-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In acetone for 10h; Heating;
  • 12
  • [ 39630-68-7 ]
  • PEG-mesylate [ No CAS ]
  • MeO-PEG5000-isophthalic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: diethyl 5-hydroxyisophthalate With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: PEG-mesylate In N,N-dimethyl-formamide at 75℃; for 20h;
  • 13
  • [ 39630-68-7 ]
  • [ 5305-40-8 ]
  • 4,6-bis[3,5-bis(ethoxycarbonyl)phenoxy]pyrimidine-5-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In tetrahydrofuran for 5h; Heating;
  • 14
  • [ 39630-68-7 ]
  • [ 100-11-8 ]
  • [ 350671-21-5 ]
YieldReaction ConditionsOperation in experiment
96.5% With potassium carbonate In acetone for 2h; Heating;
  • 15
  • [ 37860-51-8 ]
  • [ 39630-68-7 ]
  • [ 371919-09-4 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetonitrile for 16h; Heating;
  • 16
  • [ 39630-68-7 ]
  • [ 19249-03-7 ]
  • [ 186349-09-7 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetonitrile for 16h; Heating;
  • 17
  • [ 39630-68-7 ]
  • [ 74-88-4 ]
  • [ 201734-78-3 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In acetone Heating;
  • 18
  • [ 39630-68-7 ]
  • 6-azido-1-(4-methylbenzenesulfonate)hexan-1-ol [ No CAS ]
  • 5-(6-azido-hexyloxy)-isophthalic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In N,N-dimethyl-formamide
  • 19
  • [ 39630-68-7 ]
  • [ 153707-56-3 ]
YieldReaction ConditionsOperation in experiment
96% With lithium aluminium tetrahydride In tetrahydrofuran Heating;
96% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
85% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5.5h; Inert atmosphere; 1 A solution of compound 2 (21.2 g, 0.089 mol) in dry tetrahydrofuran (80 mL) was slowly added dropwise under nitrogen,LiAlH4 (10.1 g, 0.267 mol) in dry tetrahydrofuran (50 mL)The temperature is maintained at about 0 ° C. After completion of the dropwise addition, the reaction was stirred at 0 ° C for 30 minutes, then returned to room temperature, and the reaction was stirred for 5 hours.(100 mL) was slowly added dropwise, the temperature was maintained below 0 ° C, and then 1 N hydrochloric acid was slowly added dropwise to pH 3, filtered and the solid was washed with tetrahydrofuran (20 mL * 3)The filtrate was distilled under reduced pressure to remove tetrahydrofuran and the aqueous layer was extracted with dichloromethane (100 mL * 3). The organic layer was collected,Washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to give 11.7 g of compound 3 in 85% yield.
77% With lithium aluminium tetrahydride In tetrahydrofuran Heating;
With palladium 10% on activated carbon; hydrogen
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h;

  • 20
  • [ 24424-99-5 ]
  • [ 39630-68-7 ]
  • [ 918402-87-6 ]
YieldReaction ConditionsOperation in experiment
95% With dmap In dichloromethane at 0 - 20℃;
95% With dmap In dichloromethane at 20℃;
68% With dmap In dichloromethane at 0 - 20℃; for 3h; 1.4 Step 4: Preparation of 5-tert-butoxycarbonyloxycarbonyl ester diethyl isophthalate (VI) To a 500 mL round bottom flask equipped with a magnetic stirrer, diethyl 5-hydroxyisophthalate (V) (14 g, 60 mmol) and dichloromethane (200 mL) were added and stirred to 0 ° C. Then, DMAP (368 mg, 3 mmol) and di-tert-butyl dicarbonate (17.9 g, 82 mmol) were added and stirred at room temperature for 3 h. The reaction was quenched by the addition of saturated ammonium chloride solution (150 mL) to the reaction solution, and the mixture was extracted with dichloromethane (3 x 100 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated. A crude yellow solid was obtained. Recrystallization from methanol, crystal precipitation. The filter cake was washed three times with petroleum ether to give 13.3 g of a white solid in 68% yield.
  • 21
  • [ 39630-68-7 ]
  • 1,3-bis(bromomethyl)-5-benzyloxybenzene [ No CAS ]
  • [ 894094-40-7 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In acetone for 12h; Inert atmosphere; Schlenk technique; Reflux;
78% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 60h;
  • 22
  • [ 39630-68-7 ]
  • 4-amino-5-tert-butoxycarbonyloxy-isophthalic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / DMAP / CH2Cl2 / 20 °C 2: 94 percent / tetrabutylammonium fluoride / diethyl ether; tetrahydrofuran / 0.17 h / 20 °C
  • 23
  • [ 39630-68-7 ]
  • [ 923031-51-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / DMAP / CH2Cl2 / 20 °C
  • 24
  • [ 39630-68-7 ]
  • [ 819066-98-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / 0 - 20 °C 2: 90 percent / K2CO3 / acetonitrile / 24 h / Heating 3: 89 percent / CBr4; Ph3P / CH2Cl2 / 20 °C 4: 91 percent / K2CO3 / dimethylformamide 5: hydrazine hydrate / CH2Cl2; ethanol / 1 h / Heating
Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 5.5 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / Reflux 3: carbon tetrabromide; triphenylphosphine / dichloromethane / 20 °C 4: potassium carbonate / N,N-dimethyl-formamide / 5 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice
  • 25
  • [ 39630-68-7 ]
  • [ 144876-14-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / Heating 2: 35 percent / K2Cr2O7 / dimethylsulfoxide / 100 °C
  • 26
  • [ 39630-68-7 ]
  • [ 251912-48-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / K2CO3 / acetone / 10 h / Heating 2: 99 percent / LAH / tetrahydrofuran / 8 h / Heating
  • 27
  • [ 39630-68-7 ]
  • methanesulfonic acid 3-benzyloxy-5-methanesulfonyloxymethyl-benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 92 percent / K2CO3 / acetone / 10 h / Heating 2: 99 percent / LAH / tetrahydrofuran / 8 h / Heating 3: 86 percent / TEA / CH2Cl2 / 0.5 h / 0 °C
  • 28
  • [ 39630-68-7 ]
  • [ 251912-33-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / K2CO3 / acetone / 10 h / Heating 2: 99 percent / LAH / tetrahydrofuran / 8 h / Heating 3: 86 percent / TEA / CH2Cl2 / 0.5 h / 0 °C 4: 95 percent / K2CO3 / acetone / 10 h / 40 °C
  • 29
  • [ 39630-68-7 ]
  • [ 88194-15-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) t-BuOK / 1.) THF, 30 min, 2.) THF, overnight 2: 50 percent aq.NaOH / tetrahydrofuran / 1 h
  • 30
  • [ 39630-68-7 ]
  • [ 156946-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 10 min, 2.) THF, reflux, overnight 2: 66.5 percent / azoisobutyronitrile / toluene / 20 h / Heating
  • 31
  • [ 39630-68-7 ]
  • N,N'-Bis-(6-amino-pyridin-2-yl)-5-(10-mercapto-decyloxy)-isophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 10 min, 2.) THF, reflux, overnight 2: 66.5 percent / azoisobutyronitrile / toluene / 20 h / Heating 3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, a) -78 deg C, 7 h, b) RT, overnight
  • 32
  • [ 39630-68-7 ]
  • [ 113597-97-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 57 percent / K2CO3 / dimethylformamide / 12 h / 60 °C 2: NaOH / ethanol; H2O / 12 h / 65 °C 3: thionyl chloride / dimethylformamide / 8 h / Heating 4: 43 percent / 4-Angstroem molecular sieve, Et3N / CH2Cl2 / 0 deg C, 10 h; room temp., 12 h
  • 33
  • [ 39630-68-7 ]
  • [ 113597-98-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide / 48 h 2: NaOH / ethanol; H2O / 12 h / 65 °C 3: thionyl chloride / dimethylformamide / 8 h / Heating 4: 22 percent / 4-Angstroem molecular sieve, Et3N / CH2Cl2 / 0 deg C, 10 h; room temp., 12 h
  • 34
  • [ 39630-68-7 ]
  • [ 113585-44-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide / 48 h 2: NaOH / ethanol; H2O / 12 h / 65 °C 3: thionyl chloride / dimethylformamide / 8 h / Heating 4: 44 percent / 4-Angstroem molecular sieve, Et3N / CH2Cl2 / 0 deg C, 6 h; room temp., 12 h
  • 35
  • [ 39630-68-7 ]
  • [ 113585-47-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide / 48 h 2: NaOH / ethanol; H2O / 12 h / 65 °C 3: thionyl chloride / dimethylformamide / 8 h / Heating 4: 35 percent / 4-Angstroem molecular sieve, Et3N / CH2Cl2 / 0 deg C, 10 h; room temp., 12 h
  • 36
  • [ 39630-68-7 ]
  • [ 113585-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide / 48 h 2: NaOH / ethanol; H2O / 12 h / 65 °C 3: thionyl chloride / dimethylformamide / 8 h / Heating 4: 45 percent / 4-Angstroem molecular sieve, Et3N / CH2Cl2 / 0 deg C, 10 h; room temp., 12 h
  • 37
  • [ 39630-68-7 ]
  • [ 113585-35-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 48 h 2: NaOH / ethanol; H2O / 12 h / 65 °C
  • 38
  • [ 39630-68-7 ]
  • [ 19660-17-4 ]
  • [ 920271-54-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile for 4h; Heating / reflux; II Example H: Synthesis of compounds XII-XVI (and analogs):; 3-bromopropyl methacrylate and the appropriate phenol are reacted according to the following procedure: The phenol (1 mol) is dissolved in MeCN (300 mL), then anhydrous potassium carbonate (2 mol) and 3-bromopropyl methacrylate (1.1 mol) are added. The stirring mixture is heated to reflux for 4 hours, then the MeCN is removed by distillation. After cooling, petroleum ether (500 mL) is added to the resulting slurry, which is then filtered through a plug of 5 mm silica gel. The solids are washed with a further 500 mL of petroleum ether, then the combined petroleum ether fractions are gradually cooled until the product crystallizes (-20 to -50°C, depending on the compound). The product is collected by filtration, then is dried under vacuum to give an analytically pure compound at 50-90% yield.
  • 39
  • [ 894094-41-8 ]
  • [ 39630-68-7 ]
  • [ 1161867-82-8 ]
YieldReaction ConditionsOperation in experiment
88% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Inert atmosphere;
88% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 50℃; for 12.1667h; Inert atmosphere; Schlenk technique;
  • 40
  • [ 39630-68-7 ]
  • [ 98-68-0 ]
  • [ 1012984-95-0 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine In tetrahydrofuran at 0 - 25℃; Inert atmosphere;
  • 41
  • [ 39630-68-7 ]
  • [ 74-95-3 ]
  • [ 1268139-40-7 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In acetone at 60℃; for 8h;
  • 42
  • [ 35168-64-0 ]
  • [ 39630-68-7 ]
  • [ 1330184-54-7 ]
YieldReaction ConditionsOperation in experiment
90% With 15-crown-5; potassium carbonate In tetrahydrofuran at 65℃; for 24h; Inert atmosphere;
  • 43
  • [ 1194-02-1 ]
  • [ 39630-68-7 ]
  • [ 1200807-07-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; 2.2.1 Synthesis of 5-(4-carboxy-phenoxy)-isophthalic acid (H3L1) The ligand was synthesized following an earlier reported [32] procedure with slight modifications. No.7 5-Hydroxy-isophthalic acid diethyl ester (4 g, 16.8 mmol), dry No.8 K2CO3 (2.14 g, 24.12 mmol) was mixed in a 50 mL round-bottom flask under an inert atmosphere and then 10 mL of dry No.9 DMF was added to it. The mixture was stirred for a while at 80 °C followed by addition of No.10 4-fluoro-benzonitrile (2.4 g, 18.4 mmol) and the resulting mixture was stirred for 24 h in an oil-bath at 80 °C. The resulting solution was poured into ice-cold water (150 mL) whereupon a white solid precipitated that was collected by filtration and dried in air. This white solid was hydrolysed by refluxing in No.11 aqueous ethanol containing 6(N) NaOH solution (100 mL). Finally, the resulting solution was acidified with 6(N) HCl solution to obtain a white No.12 precipitate. After keeping it overnight in the freezer, it was collected by filtration and dried at 80 °C. Yield: 1.9 g (80%). This compound did not melt up to 300 °C. IR: broad peak (s) at 3555 and 3100 cm-1 corresponding to νO-H (str); sharp peak at 1722 cm-1 corresponding to νCO (str);1H NMR, δ (ppm): 7.12 (d, J = 6.8 Hz, 2H); 7.70 (s, 2H); 7.95 (d, J = 6.8 Hz, 2H); 8.24(s, 1H). Elemental Anal. Calc. for C15H10O7 (302.04): C, 59.61; H, 3.33. Found: C, 59.77; H, 3.39%. ESI-MS: m/z (100%) 302.0429 [M]+.
  • 44
  • [ 394-47-8 ]
  • [ 39630-68-7 ]
  • [ 1361345-86-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: diethyl 5-hydroxyisophthalate With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Inert atmosphere; Stage #2: 2-fluorobenzonitrile In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; 2.2.2 Synthesis of 5-(2-carboxy-phenoxy)-isophthalic acid (H3L2) The ligand was synthesized following an earlier reported [33] procedure with slight No.14 modifications.5-Hydroxyisophthalic acid diethyl ester (3.5 g, 14.7 mmol), dry No.8 K2CO3 (3.1 g, 22.1 mmol) was mixed in a 50 mL round-bottomed flask under an inert atmosphere and then 20 mL of dry No.9 DMF was added to it. The mixture was stirred for 30 min at 80 °C and treated with No.15 2-fluorobenzonitrile (1.8 mL, 16.6 mmol). The resulting mixture was then stirred for 24 h in an oil-bath at 80 °C. It was then cooled to room temperature and poured into ice-cold water (100 mL) whereupon a white solid precipitated. The solid was collected by filtration and dried in air which was further hydrolyzed by refluxing with 6(N) No.16 NaOH solution (50 mL) for 24 h. Finally, the resultant solution was carefully acidified in cold condition, with drop wise addition of 6(N) No.17 HCl to obtain a white precipitate. Keeping the flask over-night in the freezer, the white No.18 solid was collected by filtration, washed thoroughly with water and dried at 80 °C in vacuum. Yield: 2.9 g (82%). This compound did not melt up to 300 °C.IR: sharp peak at 1700 cm-1corresponding to νCO (str); 1H NMR (DMSO-d6), δ (ppm): 7.16 (d, J = 8.3 Hz, 1H); 7.33 (t, J = 7.6 Hz, 1H); 7.48 (s, 2H); 7.58-7.61 (m, 1H); 7.85 (d, J = 7.7 Hz, 1H); 8.12 (s, 1H); 13 C NMR (DMSO-d6), δ (ppm): 120.6, 122.7, 123.9, 125.4, 125.7, 131.8, 133.9, 153.6, 158.5, 166.4, 166.5. Elemental Anal. Calc. for C15H10O7 (302.04): C, 59.61; H, 3.33. Found: C, 59.74; H, 3.21%. ESI-MS: m/z (100%) 301.0427 [M-1].
  • 45
  • [ 18226-42-1 ]
  • [ 39630-68-7 ]
  • hexaethyl-5,5',5''-(benzene-1,3,5-triyltris(methylene))tris(oxy)triisophthalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In acetone at 20℃; for 24h;
  • 46
  • 1,3,5-tris((3,5-bis(bromomethyl)phenoxy)methyl)benzene [ No CAS ]
  • [ 39630-68-7 ]
  • dodecaethyl 5,5',5'',5''',5'''',5'''''-(5,5',5''-(benzene-1,3,5-triyltris(methylene))tris(oxy)tris(benzene-5,3,1-triyl))hexakis(methylene)hexakis(oxy)hexaisophthalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In acetone at 20℃; for 24h;
  • 47
  • [ 39630-68-7 ]
  • [ 110-56-5 ]
  • [ 52739-96-5 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: diethyl 5-hydroxyisophthalate With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: 1,4-dichlorobutane In N,N-dimethyl-formamide at 80℃; for 20h; Inert atmosphere; 2.2.1 Synthesis of 5,5′-(butane-1,4-diyl)-bis(oxy)-diisophthalic acid (H4L) 5-hydroxy-isophthalic acid diethyl ester (2.38g, 10mmol) and anhydrous K2CO3 (3g, 22mmol) were put in a 50mL round bottom flask under nitrogen atmosphere and treated with 20mL of dry DMF. The reaction mixture was stirred for 1h at 70°C followed by addition of 1,4-dichlorobutane (0.64g, 5mmol), and the resulting mixture was stirred for 20h in an oil-bath at 80°C. At the end of the period, the solution was allowed to cool to room temperature and then poured into ice-water (100mL) with vigorous stirring that afforded a white precipitated (tetraethyl 5,5′-(butane-1,4-diyl)-bis(oxy)-diisophthalate) which was collected by filtration, washed with water three times, and dried in air. Then the tetraethyl 5,5′-(butane-1,4-diyl)-bis(oxy) diisophthalate (2.65g, 5mmol) was hydrolyzed by refluxing it with 95% ethanol solution for 1h followed by addition of NaOH (0.8g, 20mmol) and the reaction mixture was refluxed for 15h in an oil-bath. Finally, the resulting solution was poured into ice-water (100mL) with vigorous stirring and was acidified carefully with 4M HCl to obtain a white precipitate. After keeping it overnight in the freezer, the white solid was collected by filtration and dried at air. Yield: 2.02g (96%). FT-IR (KBr, cm-1): 3096.35(s), 2961(s), 1697(s), 1597(m), 1462(m), 1402(m), 1273(m), 1126(w), 1051(m), 909(w), 759(w), 668(w), 530(w), 479(w).
Stage #1: diethyl 5-hydroxyisophthalate With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: 1,4-dichlorobutane In N,N-dimethyl-formamide at 80℃; for 20h; Inert atmosphere;
  • 48
  • [ 39630-68-7 ]
  • C10H12N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With hydrazine In ethanol for 72h; 6 2.6. 11Et A solution of 10Et (37.61 g, 161 mmol) and hydrazine monohydrate (7.9 mL, 160 mmol) in ethanol (50 mL) was stirred for 3 days. The reaction mixture was poured into water, and the precipitate was collected by filtration, washed with water followed by ethyl acetate, and dried in vacuo to give 11Et (18.07 g, 50 %) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 10.08 (s, 1H), 9.87 (s, 1H), 7.85 (t, J = 1.5 Hz, 1H), 7.48-7.43 (m, 2H), 4.49 (s, 2H), 4.31 (q, J = 7.1 Hz, 2H), 1.32 (t, J = 7.1 Hz, 3H) ppm.
  • 49
  • [ 39630-68-7 ]
  • [ 22115-41-9 ]
  • 5-(2-cyanobenzyloxy)isophthalic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: diethyl 5-hydroxyisophthalate With potassium carbonate In acetonitrile at 80℃; for 0.5h; Inert atmosphere; Stage #2: 2-(bromomethyl)benzonitrile In acetonitrile for 24h; Inert atmosphere; Reflux; 3.1 2.3.1. 5-(2-Cyanobenzyloxy)isophthalic Acid diethyl ester(o-cbiae) 5-Hydroxyisophthalic acid diethyl ester (3.5 g, 0.01 mol) anddry K2CO3 (5.1 g, 0.04 mol) were mixed in a round-bottom flaskunder an inert atmosphere. Dry acetonitrile (25 mL) was addedto it, and the mixture was stirred for 30 min at 80 C. The mixturewas treated with 2-bromomethylbenzonitrile (2.9 g, 0.01 mol), andthe resulting solution was refluxed for 24 h. After completion ofthe reaction, it was allowed to cool to room temperature andpoured in 200 mL ice-cold water to obtain an off-white solid thatwas collected by filtration and air-dried. Yield: 4.2 g (81%). Meltingpoint 74 C; IR: sharp peak at 1713 cm1 and 2229 cm1 correspondingto mCO (str) and mCN (str). 1H NMR (CDCl3, 500 MHz), d(ppm): 1.4 (t, 6H); 4.39 (q, 4H);5.32 (s, 2H); 7.48 (d, 2H); 7.66 (d,1H); 7.73(dd, 1H); 8.33 (s, 1H); 13C NMR (DMSO-d6), d (ppm):14.3, 61.6, 68.1, 111.6, 118.8, 120.1, 123.8, 128.8,129.0, 132.4,133.1, 133.2, 139.9, 158.2, 165.5.Elemental analysis: Calcd. forC20H19NO5 (353.1263): C, 67.98; H, 5.42%; N, 3.96%. Found: C,67.53; H, 5.24; N, 3.67%. ESI-MS: m/z (100%) 354.1331 [M+1]+(See Supporting Information Figs. S8-S11).
  • 50
  • [ 39630-68-7 ]
  • C25H51BrO12 [ No CAS ]
  • C37H64O17 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium carbonate In acetone for 12h; Reflux; 4 Etherification of Compound 1 Etherification of Compound 1: a three-necked flask was added compound 1 Ommo l (2.38g), acetone (1 OOmL), lOmmol potassium carbonate (1.37g), the compound lOmmol Br (CH2CH20) 12CH3 (6.23g), heated at reflux after 12 hours the reaction was concentrated to give the crude product was purified by column chromatography with dichloromethane / petroleum ether (volume ratio 3: 1) mixture as an eluent, rotary evaporated to give a white solid compound 2 (5.04g, yield: 63.0%)
  • 51
  • [ 54149-17-6 ]
  • [ 39630-68-7 ]
  • C17H24O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In acetone for 12h; Reflux; 3 Etherification of Compound 1 Etherification of Compound 1: 1 was added to the flask three Ommo a compound l (2.38g), acetone (100mL), lOmmol potassium carbonate (1 · 37g), the compound lOmmol Br (CH2CH20) 2CH3 (l .81g), heating after the reaction was refluxed for 2 hours, concentrated to give crude product was isolated by column chromatography, eluting with dichloromethane / petroleum ether (volume ratio 3: 1) mixture as an eluent, the solvent rotary evaporated to give a white solid compound 2 (2.13g, yield : 71.0%).
  • 52
  • [ 1397866-95-3 ]
  • [ 39630-68-7 ]
  • [ 123-11-5 ]
  • C48H45BF2N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.9% Stage #1: 10-(4-(chloromethyl)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine; diethyl 5-hydroxyisophthalate With 18-crown-6 ether; potassium carbonate; potassium iodide In tetrahydrofuran at 65℃; for 6h; Stage #2: 4-methoxy-benzaldehyde With piperidine; toluene-4-sulfonic acid In dichloromethane; toluene at 140℃; for 8h; 1.2 Example 1.2 (Preferred Embodiment) After the mixture of BODIPY-C (1.03 mmol) and ethyl 5-hydroxyisophthalate (1.545 mmol) in a molar ratio of 1: 1.5, 25 mL of tetrahydrofuran was added followed by K2CO3 (1.236 mmol) of KI (0.206 mmol)Eighteen crown ether six (0.1mg); which mixed heated to 65 water bath for 6 hours. After the reaction mixture was concentrated and treated with 10ml of methylene chloride was dissolved the solution was filtered at reflux trap structures, followed by 4-methoxybenzaldehyde (351.2mg, 2.575mmol), was added 20mL of toluene,The ratio of 4-methylbenzenesulfonic acid and piperidine, 4-methylbenzenesulfonic acid (0.206 mmol) and piperidine (0.515 mmol) to BODIPY-C were then 0.2: 1 and 0.5: 1, respectively,After mixing, the reaction mixture was heated to 140 ° C for 8 hours. After completion of the reaction, the reaction mixture was concentrated, and 20 mL of dichloromethane was added. The mixture was extracted with 3 × 30 mL of saturated brine and the aqueous phase was extracted with 3 × 20 mL of dichloromethane. Dried over anhydrous sodium sulfate and evaporated to give a blue-violet oil which was chromatographed on silica gel eluting with petroleum ether: ethyl acetate = 4: 1 to give a blue solid BODIPY-DBA 574.2 mg, 70.9%.
  • 53
  • [ 10420-20-9 ]
  • [ 39630-68-7 ]
  • diethyl 5-[4-(9-carbazolyl)butoxy]-1,3-benzenedicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 16h; 1.2 Diethyl 5-hydroxyisophthalate (5.33 mmol) was dissolved in 40 ml of N, N-dimethylformamide, followed by the addition of K2CO3(25 mmol).The 4C-Cz obtained in step (1) was dissolved in 13 ml of N, N-dimethylformamide, and then added dropwise to the above-mentioned diethyl 5-hydroxyisophthalate solution and reacted at 150 ° C for 16 h.The reaction solution was poured into water and extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate and distilled. The product was adsorbed onto silica gel and mixed with ethyl acetate / petroleum ether (V / V = 1: 7) Was chromatographed as an eluent to give diethyl 5- [4- (9-carbazolyl) butoxy] -1,3-benzenedicarboxylate (E1) in 51% yield.
  • 54
  • [ 39630-68-7 ]
  • C30H25BrN4O3 [ No CAS ]
  • C42H38N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;
  • 55
  • [ 23351-91-9 ]
  • [ 39630-68-7 ]
  • 56
  • [ 39630-68-7 ]
  • [ 22115-41-9 ]
  • diethyl 5-(2-cyanophenethyl)isophthalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: diethyl 5-hydroxyisophthalate With potassium carbonate In acetonitrile at 80℃; for 0.5h; Inert atmosphere; Stage #2: 2-(bromomethyl)benzonitrile In acetonitrile for 24h; Reflux; Inert atmosphere;
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