BIS (P-DIMETHYLSILYL) PHENYL ETHER

4-Bromobenzene-dimethylsilane (10.0 g, 46.5 mmol), copper iodide (44.3 mg, 0.233 mmol) and benzotriazole (55.4 mg, 0.465 mmol) were added to a flask and dimethylsulfoxide 50 mL, 5 mL / g), and the mixture was stirred at room temperature for 30 minutes, Then 4-dimethylsilanephenol (8.50 g, 55.8 mmol) and sodium tert-butoxide (6.26 g, 65.1 mmol) were added and reacted at 95-100 ° C for 18 hours with stirring.After completion of the reaction, water and EtOAc solvent were added to extract, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated.HPLC measurements were carried out with the reaction mixture to determine the proportions of impurities A and B in addition to the compound of formula 6, and the results are shown in Table 2. The reaction mixture was further purified by flash column chromatography (Pet. Ether: DCM = 5: 1), respectively, and were identified by 1H-NMR.4-Bromophenyl ether (50.0 g, 152 mmol) of the formula (7) was placed in a flask and dissolved by adding a dry THF solvent (375 mL, 7.5 mL / g). Magnesium (8.87 g, 365 mmol ) And iodine (3.85 g, 15.2 mmol) were dissolved in dry THF (25.0 mL) and slowly added dropwise. After completion of the dropwise addition, the reaction product was refluxed to synthesize the Grignard compound of formula (8).The Grignard compound of Formula 8 was placed in a flask, and the chloro-dimethylsilane compound of Formula 1 (51.0 mL, 456 mmol) was added thereto while maintaining the temperature at 0 C, followed by stirring at room temperature for 24 hours. After completion of the reaction, the reaction mixture was quenched with a saturated aqueous NH4Cl solution, extracted with an EtOAc solvent, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated.HPLC measurements were carried out with the reaction mixture to determine the proportions of impurities A and B in addition to the compound of formula 6, and the results are shown in Table 1 below.4-Bromobenzene-dimethylsilane (10.0 g, 46.5 mmol), copper iodide (44.3 mg, 0.233 mmol) and benzotriazole (55.4 mg, 0.465 mmol) were added to a flask and dimethylsulfoxide 50 mL, 5 mL / g), and the mixture was stirred at room temperature for 30 minutes, Then 4-dimethylsilanephenol (8.50 g, 55.8 mmol) and sodium tert-butoxide (6.26 g, 65.1 mmol) were added and reacted at 95-100 C for 18 hours with stirring.After completion of the reaction, water and EtOAc solvent were added to extract, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated.HPLC measurements were carried out with the reaction mixture to determine the proportions of impurities A and B in addition to the compound of formula 6, and the results are shown in Table 2. The reaction mixture was further purified by flash column chromatography (Pet. Ether: DCM = 5: 1), respectively, and were identified by 1H-NMR.Example 23Synthesis of the crosslinker 6b from 3b and bis[(p-dimethylsilyl)phenyl]ether-Bis[(p-dimethylsilyl)phenyl]ether (0.1 g, 0.349 mmol) and 3b (0.326 g, 0.698 mmol) were mixed in 2 mL of hexane in a vial and 90 muL (9.90 mumol of Pt) of the Karstedt catalyst solution was added and the mixture was mixed vigorously for 2 min using a mechanical stirrer to obtain a viscous product. FT-IR: nu (-C'C-C'C-): 2072 cm-1 and nu (-CHCH2): 1596 cm-1. DSC analysis (from RT to 400 C. at 10 C./min) in N2 of 6b: Melting endotherm at 101 C. and exotherm at 307 C.Example 20Synthesis of the crosslinker 6a from 3a and bis[(p-dimethylsilyl)phenyl]ether-Bis[(p-dimethylsilyl)phenyl]ether (0.1 g, 0.349 mmol) and 3a (0.152 g, 0.698 mmol) were mixed in 2 mL of hexane in a vial and 90 muL (9.90 mumol of Pt) of the Karstedt catalyst solution was added and the mixture was mixed vigorously for 2 min using a mechanical stirrer to obtain a viscous product. FT-IR: nu (-C'C-C'C-): 2072 cm-1 and nu (-CHCH2): 1596 cm-1.

Molecular Weight:284.50
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:284.10526833
Monoisotopic Mass:284.10526833
Topological Polar Surface Area:9.2
Heavy Atom Count:19
Complexity:226
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes