1H-Isoindol-1-one, 3-(4-chlorophenyl)-2,3-dihydro-3-hydroxy- synthesis
- Product Name:1H-Isoindol-1-one, 3-(4-chlorophenyl)-2,3-dihydro-3-hydroxy-
- CAS Number:956-92-3
- Molecular formula:C14H10ClNO2
- Molecular Weight:259.69
Yield:956-92-3 95%
Reaction Conditions:
Stage #1: bromochlorobenzenewith magnesium in tetrahydrofuran;
Stage #2: phthalimide in tetrahydrofuran;dichloromethane at 20; for 1.5 h;Inert atmosphere;
Steps:
General procedure for the synthesis of 3-aryl-3-hydroxyisoindolin-1-one
General procedure: To a solution of phthalimide (20 mmol) in CH2Cl2 (70 mL) was added the Grignard reagent (preformed from 50 mmol ArBr, 60 mmol mg in 30 mL THF) at room temperature. The resulting mixture was stirred at room temperature for 1.5 h and quenched with saturated aqueous solution of NH4Cl (40 mL). Then the mixture was extracted with ethyl acetate and washed with brine. The collected organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography, eluting with ethyl acetate/petroleum ether 1:1 (v/v), to afford the 3-aryl-3-hydroxyisoindolin-1-ones.
References:
Ge, Chen;Liang, Ren-Xiao;Liu, Ren-Rong;Xiang, Bin;Jia, Yi-Xia [Tetrahedron Letters,2017,vol. 58,# 2,p. 142 - 144] Location in patent:supporting information
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