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Ethyl-2,2-difluoro-2-(4-tert-butylphenyl)acetate synthesis

2synthesis methods
-

Yield:1027514-13-1 43%

Reaction Conditions:

with copper in dimethyl sulfoxide at 60; for 12 h;Inert atmosphere;

Steps:

General Procedure A (Synthesis of ethyl α,α-difluoroarylacetates or ethyl α-fluoroarylacetates from aryl iodides)

General procedure: To a suspension of activated Cu powder (2.6 eq.) in DMSO (0.38 M) was added the appropriate aryl iodide (1.0 eq.) and ethyl bromodifluoroacetate (1.0 eq.) or ethyl bromofluoroacetate (1.0 eq.) under nitrogen atmosphere. The reaction mixture was stirred at 60°C for 12 h. The reaction mixture was filtered through a pad of Celite and washed with Et2O. The mixture was washed with aq. NH4Cl (sat., 2x) and brine (2x), then dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography.

References:

Verhoog, Stefan;Pfeifer, Lukas;Khotavivattana, Tanatorn;Calderwood, Samuel;Collier, Thomas Lee;Wheelhouse, Katherine;Tredwell, Matthew;Gouverneur, Véronique [Synlett,2016,vol. 27,# 1,art. no. ST-2015-D0820-L,p. 25 - 28] Location in patent:supporting information