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Chemistry
Organic Building Blocks
Benzene Compounds
6,6'-((Ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-di-tert-butylphenol)
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Organic Building Blocks
Benzene Compounds

[ CAS No. 103595-81-9 ] {[proInfo.proName]}

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Chemical Structure| 103595-81-9
Chemical Structure| 103595-81-9
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Product Details of [ 103595-81-9 ]

CAS No. :103595-81-9 MDL No. :MFCD00312332
Formula : C32H48N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SSYLTCZZAVKLCT-UHFFFAOYSA-N
M.W : 492.74 Pubchem ID :1897040
Synonyms :

Safety of [ 103595-81-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 103595-81-9 ]

* 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 [ 103595-81-9 ]

[ 103595-81-9 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 37942-07-7 ]
  • [ 107-15-3 ]
  • N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.1% In methanol at 65℃; for 17h; Inert atmosphere;
87% In methanol at 65℃;
72% In methanol Reflux; 2.1.3 Synthesis of ligands General procedure: The Schiff bases used for the synthesis of the catalysts were prepared by the well known reaction between salicylaldehyde and diamine. Slight experimental variations were introduced with respect to literature methods [27] and the resulting procedure was successfully applied to a number of differently substituted aldehydes. (0015) General procedure: Two equivalents of the appropriate salicylaldehyde were dissolved in the minimum volume of boiling methanol (generally, 20 ml) and added dropwise with one equivalent of diamine (either 1,2-diaminoethane or 1,2-benzenediamine) in 5 ml methanol. The solution was refluxed until all the aldehyde disappeared (TLC analysis) and then cooled to room temperature, thus causing precipitation of the Schiff base, as a yellow solid. The filtered solid was washed with a small amount of methanol, then with diethyl ether and dried. The following Schiff bases were prepared: (0016) Salophen, [1,2-bis-(salicylideneamino)benzene]: yield 95.3%; 5,5′-Cl2salophen, [1,2-bis-(5-Cl-salicylideneamino)benzene]: yield >99%; 5,5′-(t-Bu)2salophen [1,2-bis-(5-t-Bu-salicylideneamino)benzene]: yield 75%; 3,3′-(OMe)2salophen, [1,2-bis-(3-OMe-salicylideneamino)-benzene]: yield 77%; 5,5′-(OMe)2salophen, [1,2-bis-(5-OMe-salicylideneamino)-benzene]: yield 79%; 3,3′,5,5′-Cl4salophen [1,2-bis-(3,5-Cl2salicylideneamino)benzene]: yield 95%; 3,3′,5,5′-(t-Bu)4salophen [1,2-bis-(3,5-di-t-Bu-salicylideneamino)benzene]: yield 75%. (0017) Salen, [1,2-bis-(salicylideneamino)ethane]: yield 88%; 5,5′-Cl2salen, [1,2-bis-(5-Cl-salicylideneamino)ethane]: yield 67%; 5,5′-(t-Bu)2salen, [1,2-bis-(5-t-Bu-salicylideneamino)ethane]: yield 91%; 3,3′-(OMe)2salen, [1,2-bis-(3-methoxy-salicylideneamino)ethane]: yield 92%; 5,5′-(OMe)2salen, [1,2-bis-(5-OMe-salicylideneamino)ethane]: yield 92%; 3,3′,5,5′-Cl4salen, [1,2-bis-(3,5-Cl2-salicylideneamino)ethane]: yield 70%; 3,3′,5,5′-(t-Bu)4salen, [1,2-bis-(3,5-(t-Bu)2-salicylideneamino)ethane]: yield 72%. (0018) All the compounds gave 1H NMR and UV-vis spectra consistent with the structure and with literature data [25,28-30].
In methanol
In methanol at 20℃; for 2h; Inert atmosphere;
In ethanol
In ethanol at 20℃; for 4h;
In methanol; ethanol at 20℃; Inert atmosphere;
In methanol Reflux; General procedure: Two equivalents of the appropriate salicylaldehyde were dissolved in the minimum volume of boiling methanol and one equivalent of 1,2-diaminoethane in 5 mL methanol was added dropwise. The solution was refluxed until all the aldehyde disappeared and then cooled to room temperature, thus causing precipitation of the Schiff base as a yellow solid. The filtered solid was washed with a small amount of methanol, then with diethyl ether and dried.
In ethanol
In ethanol Synthesis of Schiff bases and Mn(III)-complexes General procedure: Schiff base ligands and their corresponding complexes [NN-bis-(3,5-di-tert-butylsalicylidene)-ethylendiamine]manganese(III)chloride [Mn(3,5-dtSALEN)Cl)] (I) and [NN-bis-(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine]manganese(III)chloride [Mn(3,5-dtSALHD)Cl] (II) were prepared adopting amethodology widely reported in the literature [13,19,38-40].The ligands were prepared by condensation of 3,5-di-tert-butylsalicylaldehyde with the corresponding diamine (either,ethylenediamine or 1,2-cyclohexanediamine) in a molar ratio 1:2in ethanol. Complexes (I) and (II) were obtained then by addinga saturated solution prepared with 3.66 mmol of manganeseacetate in absolute ethanol to 1.83 mmol of the correspondingligand dissolved in 25 cm3of the same solvent pre-heated at353 K under reflux; air was slowly and shortly (10-20 s) bubbledthrough the reacting mixture since long oxidation might leadto form oxo-Mn(V) species easily detected by darkening of thebrownish solution [41], which inactivate the catalytic responseof the complexes in the targeted reaction. Then, the air streamwas stopped and the heating was kept along one extra hour withdarkening of the yellow-orange solution to brown. Afterwards,5.29 mmol of lithium chloride in ethanol were added to achieve theaccess of Cl into the coordination sphere of the transition metal,and the mixture was heated further 30 min. The resulting solidwas then dissolved in dichloromethane and refined employingthe method from Cubillos et al. [40] by means of liquid extractionwith n-heptane. The final solid was recovered by vacuum filtering and filteringand then dried at room temperature in a desiccator. The sameprocedure was used to prepare both complexes
In ethanol at 100℃; Schlenk technique; Glovebox; Inert atmosphere;
In ethanol at 80℃; for 12h; 2 0.6 g of 1, 2-ethanediamine is dissolved in 20mL of ethanol, obtained 1, 2-ethanediamine solution; 4.7 g of 3,5-di-tert-butyl salicylaldehyde is dissolved in 30mL of ethanol, obtained 3,5-di-tert-butyl salicylaldehyde solution, 3,5-di-tert-butyl salicylaldehyde is slowly added drop-wise to the 1,2-ethanediamine solution, the obtained mixed solution is refluxed at 80 ° C for 12 h, and then obtained reaction mixture. The solvent in the reaction mixture is removed by filtration; the resulting reaction product is re-crystallized from ethanol and then obtained Schiff base ligand. In the present invention, the obtained Schiff base compound is subjected to elemental analysis, and obtained the content of each atom, the results are as follows: Elem.Anal. (%):Calcd.C 78.00, H9.82, N 5.69; Found C 77 · 58, Η 9.88, N 5.77. This means, The Schiff base ligand which is obtained in this example has the structure represented by the formula (II), among them, Y for 1, 2-ethyl; R for Tert-butyl.
In ethanol
10.12 g In ethanol Reflux; 2.2.1 Synthesis ofL1, L2 andL3 Ligands General procedure: For the synthesis of L1, 1.4 mL ethylenediamine(20mmol) was added to a solution of 4.5mL salicylaldehyde(41mmol) with 50mL ethanol in a round bottomflask. The reaction mixture was thoroughly stirredat refluxing temperature for 3-4h, or until flaky yellowcrystals were formed, and the solution was then left to coolin an ice-bath. The crystals were fltered and washed, thenair-dried. Yield of L1 was found to be 5.2g. For the synthesisof L2, 7.31g 3-tert-butyl-2-hydroxybenzaldehyde;and for L3, 9.6g 3,5-di-tert-butyl-2-hydroxybenzaldehydewas taken in place of salicylaldehyde. The yield of L2 andL3 were obtained 8.23g and 10.12g, respectively.

Reference： [1]Boyle, Timothy J.; Sears, Jeremiah M.; Greathouse, Jeffery A.; Perales, Diana; Cramer, Roger; Staples, Orion; Rheingold, Arnold L.; Coker, Eric N.; Roper, Todd M.; Kemp, Richard A. [Inorganic Chemistry, 2018, vol. 57, # 5, p. 2402 - 2415]
[2]Bhunia, Asamanjoy; Gotthardt, Meike A.; Yadav, Munendra; Gamer, Michael T.; Eichhoefer, Andreas; Kleist, Wolfgang; Roesky, Peter W. [Chemistry - A European Journal, 2013, vol. 19, # 6, p. 1986 - 1995]
[3]Coletti; Galloni; Sartorel; Conte; Floris [Catalysis Today, 2012, vol. 192, # 1, p. 44 - 55]
[4]Kasumov, Veil T.; Koeksal, Fevzi [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2005, vol. 61, # 1-2, p. 225 - 231]
[5]Location in patent: experimental part Hwang, Kyu Young; Kim, Hyoseok; Lee, Yoon Sup; Lee, Min Hyung; Do, Youngkyu [Chemistry - A European Journal, 2009, vol. 15, # 26, p. 6478 - 6487]
[6]Location in patent: scheme or table Ulusoy, Mahmut; Birel, Oezguel; Ahin, Onur; Bueyuekguengoer, Orhan; Cetinkaya, Bekir [Polyhedron, 2012, vol. 38, # 1, p. 141 - 148]
[7]Lin, Wei; Dou, Guo-Lan; Hu, Ming-Hua; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing [Organic Letters, 2013, vol. 15, # 6, p. 1238 - 1241]
[8]Lee, Young Eun; Cao, Trung; Torruellas, Carilyn; Kozlowski, Marisa C. [Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 6782 - 6785]
[9]Galloni, Pierluca; Coletti, Alessia; Floris, Barbara; Conte, Valeria [Inorganica Chimica Acta, 2014, vol. 420, p. 144 - 148]
[10]Mathavan, Alagarsamy; Ramdass, Arumugam; Ramachandran, Mohanraj; Rajagopal, Seenivasan [International Journal of Chemical Kinetics, 2015, vol. 47, # 5, p. 315 - 326]
[11]Garcia, Ana M.; Moreno, Viviana; Delgado, Sonia X.; Ramírez, Alfonso E.; Vargas, Luis A.; Vicente, Miguel Á.; Gil, Antonio; Galeano, Luis A. [Journal of Molecular Catalysis A: Chemical, 2016, vol. 416, p. 10 - 19]
[12]Hsu, Chiao-Yin; Tseng, Hsi-Ching; Vandavasi, Jaya Kishore; Lu, Wei-Yi; Wang, Li-Fang; Chiang, Michael Y.; Lai, Yi-Chun; Chen, Hsing-Yin; Chen, Hsuan-Ying [RSC Advances, 2017, vol. 7, # 31, p. 18851 - 18860]
[13]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN107033193, 2017, A Location in patent: Paragraph 0088; 0089
[14]Kavitha; Subramaniam [Polyhedron, 2020, vol. 175]
[15]Tripathi, Deependra; Singh, Raj K. [Catalysis Letters, 2021, vol. 151, # 3, p. 713 - 719]
  • 2
  • [ 6156-78-1 ]
  • lithium chloride [ No CAS ]
  • N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediamine [ No CAS ]
  • [ 172172-24-6 ]
YieldReaction ConditionsOperation in experiment
75% In ethanol Mn- and org.-compds. reaction in solvent, pptn. by solid LiCl addn.; dissolving in CH2Cl2, recrystallization after hexane addn.; elem anal.;
In ethanol at 79.84℃; Reflux; Synthesis of Schiff bases and Mn(III)-complexes General procedure: Schiff base ligands and their corresponding complexes [NN-bis-(3,5-di-tert-butylsalicylidene)-ethylendiamine]manganese(III)chloride [Mn(3,5-dtSALEN)Cl)] (I) and [NN-bis-(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine]manganese(III)chloride [Mn(3,5-dtSALHD)Cl] (II) were prepared adopting amethodology widely reported in the literature [13,19,38-40].The ligands were prepared by condensation of 3,5-di-tert-butylsalicylaldehyde with the corresponding diamine (either,ethylenediamine or 1,2-cyclohexanediamine) in a molar ratio 1:2in ethanol. Complexes (I) and (II) were obtained then by addinga saturated solution prepared with 3.66 mmol of manganeseacetate in absolute ethanol to 1.83 mmol of the correspondingligand dissolved in 25 cm3of the same solvent pre-heated at353 K under reflux; air was slowly and shortly (10-20 s) bubbledthrough the reacting mixture since long oxidation might leadto form oxo-Mn(V) species easily detected by darkening of thebrownish solution [41], which inactivate the catalytic responseof the complexes in the targeted reaction. Then, the air streamwas stopped and the heating was kept along one extra hour withdarkening of the yellow-orange solution to brown. Afterwards,5.29 mmol of lithium chloride in ethanol were added to achieve theaccess of Cl into the coordination sphere of the transition metal,and the mixture was heated further 30 min. The resulting solidwas then dissolved in dichloromethane and refined employingthe method from Cubillos et al. [40] by means of liquid extractionwith n-heptane. The final solid was recovered by vacuum filtering and then dried at room temperature in a desiccator. The sameprocedure was used to prepare both complexes.
Reference： [1]Skarzewski, Jacek; Gupta, Anil; Vogt, Andrzej [Journal of Molecular Catalysis A: Chemical, 1995, vol. 103, p. 63 - 68]
[2]Garcia, Ana M.; Moreno, Viviana; Delgado, Sonia X.; Ramírez, Alfonso E.; Vargas, Luis A.; Vicente, Miguel Á.; Gil, Antonio; Galeano, Luis A. [Journal of Molecular Catalysis A: Chemical, 2016, vol. 416, p. 10 - 19]
  • 3
  • [ CAS Unavailable ]
  • [ 103595-81-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
88% With triethyl amine In toluene deaerated toluene was added to the mixt. of complex and diimine under Ar, N(C2H5)3 was added, the mixt. was heated to reflux for 22 h, allowed to cool (Ar); filtered, rotary evapd., chromd. on silica gel (CH2Cl2); elem. anal.;
Reference： [1]Works, Carmen F.; Jocher, Christoph J.; Bart, Gwen D.; Bu, Xianhui; Ford, Peter C. [Inorganic Chemistry, 2002, vol. 41, # 14, p. 3728 - 3739]
  • 4
  • [ CAS Unavailable ]
  • [ 103595-81-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
72% In ethanol addn. of 1 equiv. of Co(OAc)2*4H2O to 1 equiv. of N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediamine in hot ethanol under Ar for a few minutes; stirring at room temp. for 3 h; filtration, drying under vac., recrystn. from CH2Cl2/EtOH (v/v, 1/3); elem. anal.;
10.04 g In ethanol; lithium hydroxide monohydrate for 3h; Inert atmosphere; Reflux; 2.2.2 Synthesis ofCoL1, CoL2 andCoL3 Complexes General procedure: Three cobalt(II)-salen complexes (CoL1, CoL2 and CoL3)have been synthesized using ethanol as solvent for ligandsand water for metal salt then refluxing this mixture [34]. Inthis typical procedure, 4.02g (15mmol) L1 was taken in around-bottom flask containing a stirring-bar, and fitted witha reflux condenser and 100mL of ethanol was added undernitrogen. In a separate flask, 3.73g (15mmol) cobalt(II)acetate tetrahydrate was dissolved in 20mL water with stirringat room temperature under nitrogen. The ligand solutionwas added with the help ofa syringe, and swirled at therefluxing temperature for 3h. The dark colour precipitateformed which was filtered and dried in an oven at 70°C.The yield of N,N-bis(salicylidene)ethylenediaminocobalt(II)(CoL1) obtained was 7.54g. Similarly, the N,N-bis(3-tertbutyl-2-hydroxybenzaldene) ethylenediaminocobalt(II)(CoL2) and N,N-bis (3,5-di-tert-butyl-2-hydroxybenzaldene)ethylenediaminocobalt(II) (CoL3) were synthesizedby taking 5.71g of L2 and 7.39g of L3 respectively withobtained yield as 7.83g and 10.04g, respectively.
In methanol; toluene at 0 - 20℃; for 0.75h; Inert atmosphere;
Reference： [1]Dogan; Ulusoy; Oeztuerk; Kaya; Salih [Journal of Thermal Analysis and Calorimetry, 2009, vol. 96, # 1, p. 267 - 276]
[2]Tripathi, Deependra; Singh, Raj K. [Catalysis Letters, 2021, vol. 151, # 3, p. 713 - 719]
[3]Dadashi-Silab, Sajjad; Stache, Erin E. [Journal of the American Chemical Society, 2022, vol. 144, # 29, p. 13311 - 13318]
  • 5
  • [ CAS Unavailable ]
  • [ 103595-81-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediamine With sodium hydride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Reflux; Stage #2: iron(III) chloride In tetrahydrofuran for 4h; Inert atmosphere; Reflux;
In methanol at 25℃; for 10h; Inert atmosphere; 7 Under inert gas protection conditions, 1 g of the Schiff base ligand which is obtained in Example 2 is mixed with 0.4 g of ferric trichloride after that, add 20mL of methanol to mix and stir, the resulting mixed solution is allowed to react at 25 ° C for 10 h, after completion of the reaction the reaction system was filtered to remove the solvent, re-crystallization of Dichloromethane / methanol; and then obtained Schiff base iron complexes.
With trimethylamine In methanol Inert atmosphere;
Reference： [1]Liao, Saihu; List, Benjamin [Advanced Synthesis and Catalysis, 2012, vol. 354, # 13, p. 2363 - 2367]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN107033193, 2017, A Location in patent: Paragraph 0099; 0100
[3]Duan, Ranlong; Hu, Chenyang; Li, Xiang; Pang, Xuan; Sun, Zhiqiang; Chen, Xuesi; Wang, Xianhong [Macromolecules, 2017, vol. 50, # 23, p. 9188 - 9195]
  • 6
  • [ CAS Unavailable ]
  • [ 103595-81-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
72% With oxygen In methanol at 20℃; 2.1.4 Synthesis of VIV complexes General procedure: The synthesis of these complexes was accomplished by a procedure slightly different form that reported in the literature [31,32]. A number of the vanadium derivatives used in the literature were tested as precursors, i.e. VO(acetylacetonate)2 [31], vanadyl sulfate di-hydrate [29,33], and V(acetylacetonate)3 [34]. The best results were obtained with VIII(acac)3, in terms of reproducibility of the reaction and solubility of complexes. (0020) General procedure: The Schiff base was dissolved in 100 ml of boiling methanol, or suspended when scarcely soluble. The equimolar amount of V(acac)3 was completely dissolved in the minimum volume of MeOH with the help of sonication and added dropwise to the solution (or to the suspension), causing immediate color change from yellow to green. After an overnight stirring in an open vessel at room temperature, the reaction was stopped and the precipitated solid was collected, washed with diethyl ether, and dried. No trace of Schiff base was present. Eventually unreacted V(acac)3 was washed off with warm acetone. (0021) The following VIVO complexes were prepared, their purity was checked with TLC and HPLC analyses. (0022) SalophenVIVO, yield 73%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 242 (40,000), 314 (22,000) and 396 (18,000); 5,5′-Cl2salophenVIVO, yield 78%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 305 (12,000), 409 (10,700); 5,5′-(t-Bu)2salophenVIVO, yield 82%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 246 (40,900), 318 (22,700), 409 (15,400); 3,3′-(OMe)2salophenVIVO, yield 79%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 221 (42,000), 301 (24,000), 313 (22,000) and 335 (13,000); 5,5′-(OMe)2salophenVIVO, yield 87%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 216 (70,000), 243 (41,000), 289 (30,000), 300 (32,000), 337 (26,000) and 434 (9000); 3,3′,5,5′-Cl4SalophenVIVO: yield 78%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 315 (9800), 412 (10,000); 3,3′,5,5′-(t-Bu)4salophenVIVO, yield 87%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 250 (43,300), 327 (25,900), 416 (16,100). (0023) SalenVIVO, yield 89%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 242 (39,000), 277 (18,000) and 362 (7900); 5,5′-Cl2salenVIVO, yield 67% UV-vis in MeCN [λmax, nm] 248 (49,000), 280 sh, 370 (7400); 5,5′-(t-Bu)2salenVIVO, yield 67%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 246 (56,000), 278 (27,000), 370 (9200); 3,3′-(OMe)2salenVIVO, yield 93%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 224 (16,000), 296 (14,000) and 381 (2800); 5,5′-(OMe)2salenVIVO, yield 86%, UV-vis in MeCN [λmax, nm (ɛ, M-1 cm-1)] 251 (20,000), 286 sh (8800) and 392 (9000); 3,3′,5,5′-Cl4salenVIVO, yield 70%, UV-vis in MeCN: λmax = 370 nm (does not dissolve completely); 3,3′,5,5′-(t-Bu)4salenVIVO, yield 72%, UV-vis in CH2Cl2 [λmax, nm (ɛ, M-1 cm-1)] 252 (41,000), 288 (27,000) and 386 (3600). UV-vis spectra are consistent with literature data [35,36].
Reference： [1]Coletti; Galloni; Sartorel; Conte; Floris [Catalysis Today, 2012, vol. 192, # 1, p. 44 - 55]
  • 7
  • [ 32315-10-9 ]
  • [ 103595-81-9 ]
  • [ 1426162-56-2 ]
YieldReaction ConditionsOperation in experiment
78% With samarium; titanium tetrachloride In tetrahydrofuran for 2h; Inert atmosphere; Reflux; diastereoselective reaction;
Reference： [1]Lin, Wei; Dou, Guo-Lan; Hu, Ming-Hua; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing [Organic Letters, 2013, vol. 15, # 6, p. 1238 - 1241]
  • 8
  • [ 693-04-9 ]
  • [ 103595-81-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediamine With n-butyllithium In tetrahydrofuran-d8; hexane at -40 - 20℃; for 2h; Glovebox; Cooling; Inert atmosphere; Stage #2: butyl magnesium bromide In tetrahydrofuran-d8; hexane at 20℃; for 16h; Glovebox; Inert atmosphere; Formation of complexes 2 and 3 in THF-d8 General procedure: In a glovebox, a J. Young NMR tube containing a solution of ligand 1 (0.1mmol) in THF-d8 (0.75mL) was placed in a freezer for 1h. A solution of n-BuLi (2.5M in hexane, 0.2mmol) was then added dropwise. After 1h of stirring at room temperature, the J. Young tube was placed again in the freezer. After 1h, a solution of RMCl (0.1mmol) was added dropwise and NMR analyses were recorded after 16h at room temperature.
Reference： [1]Char, Joëlle; Brulé, Emilie; Gros, Philippe C.; Rager, Marie-Noelle; Guérineau, Vincent; Thomas, Christophe M. [Journal of Organometallic Chemistry, 2015, vol. 796, p. 47 - 52]
  • 9
  • [ CAS Unavailable ]
  • [ 103595-81-9 ]
  • [ 2340265-12-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In toluene at 40℃; for 2.5h; Inert atmosphere; 1 Synthesis of Compound [51] Under a nitrogen atmosphere,15.0 g (30 mmol) of N, N'-bis (3,5-di-tert-butylsalicylidene) -1,2 ethylenediamine,Boron trifluoride-ether complex21.6g (152mmol), 300ml toluene,20 g (152 mmol) of N, N-diisopropylethylamine was stirred with heating at 40 ° C for 2.5 hours.Cool to room temperature, add 300ml of water, and separate the filtrate into organic and aqueous layers.The organic layer was washed twice with a saturated sodium carbonate aqueous solution and dried over magnesium sulfate.The obtained solid was recrystallized from toluene (150 ml) and ethanol (750 ml),This gave 17.89 g of crude product.The crude product is under pressure 3 × 10-3Pa,Sublimation at a temperature of 220 ° C gave compound [51] (light yellow solid).
Reference： [1]Current Patent Assignee: TORAY INDUSTRIES INC - TW2019/25212, 2019, A Location in patent: Paragraph 0109; 0110

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