ChemicalBook CAS DataBase List TRIPHENYLFLUOROSILANE

TRIPHENYLFLUOROSILANE synthesis

12synthesis methods

Product Name:TRIPHENYLFLUOROSILANE
CAS Number:379-50-0
Molecular formula:C18H15FSi
Molecular Weight:278.4

455-32-3
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$25.89/5g

150-76-5 Synthesis

150-76-5
818 suppliers
$5.00/5 g

789-25-3 Synthesis

789-25-3
219 suppliers
$6.00/1g

1523-19-9
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379-50-0
121 suppliers
$84.00/5g

Yield: 96% ， 87%

Reaction Conditions:

with hydridotetakis(triphenylphosphine)rhodium(I);1,2-bis-(diphenylphosphino)ethane in chlorobenzene at 20; for 3 h;Inert atmosphere;

Steps:

4.6. The Synthesis of Esters from Benzoyl Fluoride 2 and 4-Methoxyphenol Using Triphenylsilane (Scheme 3)
In a two-necked flask equipped with a reflux condenser were placed 2 (0.5 mmol, 54 mL), 4-methoxyphenol (0.5 mmol, 62 mg), triphenylsilane (0.5 mmol, 130 mg), RhH(PPh₃)₄ (1 mol%, 5.8 mg), 1,2-bis(diphenylphosphino)ethane (2 mol%, 4.0 mg) in chlorobenzene (1 mL) under an argon atmosphere, and the solution was stirred at room temperature for 3 h. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving p-methoxyphenyl benzoate (109.1 mg, 96%) and triphenylsilyl fluoride (121.1 mg, 87%) as colorless solid. Triphenylsilyl Fluoride Colorless solid. Mp. 64.0-65.0 °C (hexane). Lit.⁸ 64 °C. ¹H-NMR (400 MHz, CDCl₃) d 7.41 (6H, t, J = 7.6 Hz), 7.48 (3H, t, J = 7.6 Hz), 7.65 (6H, dd, J = 7.6, 1.6 Hz). ¹³C-NMR (100 MHz, CDCl₃) d 128.1, 130.8, 132.5 (d, J = 16.7 Hz), 135.0 (d, J = 2.3 Hz). IR (KBr) v 3051, 3025, 1429, 1124, 841 cm^-1. MS (EI) m/z 278 (M⁺, 100%), 201 (M⁺-C₆H₅, 41%). HRMS Calcd for C₁₈H₁₅SiF: 278.0948. Found: 278.0927.

References:

Arisawa, Mieko;Igarashi, Yui;Kobayashi, Haruki;Yamada, Toru;Bando, Kentaro;Ichikawa, Takuya;Yamaguchi, Masahiko [Tetrahedron,2011,vol. 67,# 40,p. 7846 - 7859] Location in patent:supporting information; experimental part