ChemicalBook CAS DataBase List [[difluoro(triMethylsilyl)Methyl]thio]-Benzene

[[difluoro(triMethylsilyl)Methyl]thio]-Benzene synthesis

5synthesis methods

Product Name:[[difluoro(triMethylsilyl)Methyl]thio]-Benzene
CAS Number:536975-49-2
Molecular formula:C10H14F2SSi
Molecular Weight:232.37

[difluoro(phenylthio)methyl]trimethylsilane (PhSCF2SiMe3) was prepared for the first time by Prakash et al.,1 using the Barbier coupling reaction of bromodifluoromethylphenyl sulfide,2 prepared from dibromodifluoromethane and sodium benzenethiolate,3 magnesium metal, and chlorotrimethylsilane (TMSCl) in DMF (eq 1).

81290-20-2 Synthesis

81290-20-2
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$13.00/1g

108-98-5
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$26.30/10g

[[difluoro(triMethylsilyl)Methyl]thio]-Benzene

536975-49-2
18 suppliers
$100.00/100mg

Yield:536975-49-2 99%

Reaction Conditions:

Stage #1: thiophenolwith lithium tetrafluoroborate;lithium hydride in N,N-dimethyl-formamide at 25; for 0.0833333 h;Inert atmosphere;
Stage #2: (trifluoromethyl)trimethylsilane in N,N-dimethyl-formamide at 25;Inert atmosphere;

Steps:

[Difluoro(phenylsulfanyl)methyl]trimethylsilane (4)

Thiophenol (12.5g, 113.46mmol) is slowly added to a round-bottomed flask containing a mixture of LiBF₄ (12.76g, 136.15mmol) and LiH (1.08g, 136.15mmol) in DMF (560mL). The resulting mixture was stirred for 5 min more under inert atmosphere. Addition of TMSCF₃ (16.77mL, 113.46mmol) was followed by a vigorous stirring until the reaction went to completion (¹⁹F NMR check, needed approximately 15-30min). Then the reaction mixture is diluted with Et₂O and filtered over a pad of silica. The filtered mixture is extracted (Et₂O x3) and the organic layers collected and washed with water and brine. Removal of the organic solvent under vacuum gave the expected compound 4 (26.13g) in 99% yield. ¹H NMR: δ=7.61 (m, 2H), 7.42-7.34 (massif, 3H), 0.23 (m, 9H). ¹³C NMR: δ=136.4 (t, J=1Hz), 134.3 (t, J=300Hz), 129.3, 128.9, 126.2 (t, J=4Hz), -4.0 (t, J=1Hz). ¹⁹F NMR: δ=-88.04 (s, 2F).

References:

Ismalaj, Ermal;Billard, Thierry [Journal of Fluorine Chemistry,2017,vol. 203,p. 215 - 217]