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[ CAS No. 79060-88-1 ]

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Chemical Structure| 79060-88-1
Chemical Structure| 79060-88-1
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CAS No. :79060-88-1 MDL No. :MFCD00043323
Formula : C32H12BF24Na Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :886.20 g/mol Pubchem ID :23681909
Synonyms :

Safety of [ 79060-88-1 ]

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

Application In Synthesis of [ 79060-88-1 ]

  • Upstream synthesis route of [ 79060-88-1 ]
  • Downstream synthetic route of [ 79060-88-1 ]

[ 79060-88-1 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
82% With magnesium; ethylene dibromide In diethyl ether at 20℃; Inert atmosphere; Heating A three-neck round bottom flask fitted with a reflux condenser was evacuated, flame dried and filledwith argon prior to use. 1.01 g (41.7 mmol) magnesium, 0.72 g (6.4 mmol, 1 eq) NaBF4 and diethylether (150 mL) were added. To start to reaction 1.07 g (0.49 ml, 5.7 mmol, 0.9 eq) dibromoethanewere added and the flask was heated for several minutes followed by the dropwise addition of 1.71 g(6.25 ml, 36 mmol) 3,5-bis(trifluoromethyl)bromobenzene diluted with diethyl ether (50 mL) over30 min. When the exothermic reaction slowed the reaction mixture was heated for additional 30 min.The solution was then stirred over night at room temperature. The reaction mixture was quenched bythe addition of 16 g Na2CO3 in distilled water (200 mL), stirred for 30 min and filtered. The aqueousphase was extracted three times with diethyl ether (50 mL), the combined organic phases were driedover sodium sulfate and charcoal followed by filtration. The solvent was removed and the remainingcrude product was dissolved in toluene (200 mL) to remove the water with a Dean Stark trap byazeotropic distillation. The solvent was removed, the product filtered, washed with dry toluene anddried under vacuo. The product was observed as colorless solid (4.65 g, 5.3 mmol, 82 percent).m.p. decomposition >290 °C.1H-NMR (300 MHz, DMSO-d6): δ = 7.67 (s, 4H, B-p-CH), 7.61 (s, 8H, B-o-CH) ppm.13C-NMR (75.5 MHz, DMSO-d6): δ = 161.0 (q, JB = 50 Hz, 4 Ci-B), 134.0 (s, 8 B-o-CH), 128.5 (qq,JF = 31 Hz, JB = 2.7 Hz, 8 Ci-CF3), 124.0 (q, JF = 272 Hz, CF3), 117.6 (m, 4 B-p-CH) ppm.19F-NMR (283 MHz, DMSO-d6): δ = -57.6 (CF3) ppm.Elemental analysis for C32H12BF24Na*1.8 H2O: calcd. C = 41.61 H = 1.70, found C = 41.57, H = 1.66.
Reference: [1] Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369
[2] Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369
[3] Tetrahedron Letters, 2016, vol. 57, # 31, p. 3453 - 3456
[4] Organic Syntheses, 2008, vol. 85, p. 248 - 266
[5] Journal of the American Chemical Society, 2001, vol. 123, # 44, p. 11020 - 11028
[6] Organometallics, 1992, vol. 11, p. 3920 - 3922
[7] Organometallics, 2005, vol. 24, # 14, p. 3579 - 3581
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 40, p. 13335 - 13338[9] Angew. Chem., 2018, vol. 130, p. 13519 - 13522,4
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YieldReaction ConditionsOperation in experiment
47%
Stage #1: With magnesium; ethylene dibromide In diethyl ether at 20℃; Heating / reflux
Stage #2: for 0.5 h;
f) Preparation of Sodium tetrakis [3,5-bis-(trifluoromethyl)-phenyl]-borate (as described by D. L. Reger, T. D. Wright, C. A. Little, J. J. S. Lamba, M. D. Smith in Inorg. Chem., 2001, 40, 3810-3814); Step f-1: A total of 3.49 g (31.7 mmol, 1 eq.) of sodium tetrafluoroborate, 4.98 g (205 mmol, 6.45 eq.) and 600 mL of anhydrous ether were charged in a 2 L 4 neck round bottom flask, equipped with overhead stirrer, addition funnel, thermocouple, condenser, nitrogen line and heating mantle. Dibromoethane (1 mL) was added, and the flask was gently heated to initiate the reaction. The heat was removed, and a solution of 50.94 g (174 mmol, 5.47 eq.) of 3,5-bis-(trifluoromethyl)-bromobenzene in 100 mL of ether was added dropwise within 30 min, which caused the solution to gently reflux. Once all bromide was added, the reaction was heated with a heating mantle to continue the reflux for an additional 1 hour. The heat than was removed, and the resulted mixture stirred overnight at room temperature. After this period of time, the reaction mixture was poured on a cold solution of sodium carbonate (77 g of Na2CO3 in 950 mL of water) and stirred for 30 min. The top brown organic layer was separated, and the bottom milky aqueous layer was extracted with ether (2.x.300 mL). Combined organic phases were dried over sodium sulfate and stirred with 17 g of charcoal for 2 hours at room temperature. The mixture was filtered through the Celite pad, and the ether was removed on a rotovap to yield 32.4 g of brown semisolid. The obtained crude product was dissolved in 800 mL of benzene and water was removed with a Dean-Stark trap by azeotropic distillation for 3 hours. The solvent volume was reduced to about 200 mL and the residue was cooled on an ice bath to form a mixture of a solid and heavy brown oil. The heterogeneous mixture was filtered off, washed with benzene (3.x.50 mL) followed by hexane wash (1.x.100 mL). The isolated solid was dried under suction and nitrogen flow to yield 13.28 (47percent yield) of white solid with Rf=0.15 in EtOAc.
Reference: [1] Patent: US2007/27329, 2007, A1, . Location in patent: Page/Page column 7
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 44, p. 11020 - 11028
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Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4738 - 4742
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 776 - 781[2] Angew. Chem., 2017, vol. 129, p. 794 - 799,6
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