Yield:31011-26-4 46%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 20;

Steps:

4.6.3.1 General procedure for electrophilic aromatic substitutions

General procedure: The substituted chlorobenzene 1.1mmol, (1eq) was dissolved in anhydrous DMF (2.5mL) and the phenol component (1.1mmol, 1eq) was added. Cesium carbonate (1.3mmol, 1.15eq) was then added, and the reaction was allowed to proceed at room temperature until TLC indicated completion. Upon completion, the reaction mixture was filtered to remove the cesium carbonate, acidified with the addition of 1N HCl and extracted with CH₂Cl₂. The organic layers were washed with brine and dried with Na₂SO₄. Typically, the crude products were recrystallized from iPrOH or EtOAc, and the yield and characterization is reported for only the first crop of crystals. Where recrystallizations failed, products were purified by silica gel chromatography as indicated.

References:

Makley, Leah N.;Johnson, Oleta T.;Ghanakota, Phani;Rauch, Jennifer N.;Osborn, Delaney;Wu, Taia S.;Cierpicki, Tomasz;Carlson, Heather A.;Gestwicki, Jason E. [Bioorganic and Medicinal Chemistry,2021,vol. 34]