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ChemicalBook CAS DataBase List Allyl phenyl sulfone
16212-05-8

Allyl phenyl sulfone synthesis

9synthesis methods
The Preparative Method of Allyl phenyl sulfone: from Allyl Bromide and benzenesulfinate in ethanol according to the original procedure is most straightforward and avoids the use of strong-smelling thiols.
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Yield: 92%

Reaction Conditions:

Stage #1:PVS with tetraethylammoniumcyanide in dichloromethane for 0.0833333 h;
Stage #2:allyl bromide in dichloromethane at 20;

Steps:

General Procedure for the Synthesis of Sulfones 2a–m
General procedure: Vinyl sulfone (0.4 mmol) and tetraethylammonium cyanide(1.05 equiv, 0.42 mmol) were dissolved in DCM (1 mL). Thereaction mixture was stirred for 5 min, and a solution of an appropriate electrophile (1.05 equiv, 0.42 mmol) in DCM (0.5mL) was added dropwise. The resultant reaction mixture wasstirred at room temperature. After completion of the reaction(checked by crude 1H NMR or GC–MS), water (10 mL) was addedto the reaction mixture, and the product was extracted withethyl acetate (3 × 10 mL). The combined organic layers werewashed with brine (10 mL), dried over anhydrous Na2SO4, andconcentrated under vacuum. The crude product thus obtainedwas purified by column chromatography using 10–20percent ethylacetate in petroleum ether.

References:

Lee, Ji-Woong;Roy, Tamal [Synlett,2020,vol. 31,# 5,p. 455 - 458]

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