ChemicalBook CAS DataBase List Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate synthesis

4synthesis methods

Product Name:Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate
CAS Number:79060-88-1
Molecular formula:C32H12BF24Na
Molecular Weight:886.2

13755-29-8 Synthesis

13755-29-8
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$6.00/25g

328-70-1
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$10.00/25 g

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

79060-88-1
143 suppliers
$9.00/250mg

Yield:79060-88-1 82%

Reaction Conditions:

with magnesium;ethylene dibromide in diethyl ether at 20;Inert atmosphere;Heating;

Steps:

Synthesis of sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate NaB[3,5-(CF3)2C6H3]4
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 %).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.

References:

Kaliner, Maria;Strassner, Thomas [Tetrahedron Letters,2016,vol. 57,# 31,p. 3453 - 3456] Location in patent:supporting information

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328-70-1
418 suppliers
$10.00/25 g