ChemicalBook CAS DataBase List 5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE

5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE synthesis

9synthesis methods

Product Name:5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE
CAS Number:773-91-1
Molecular formula:C9H6FNO2
Molecular Weight:179.15

116176-92-2 Synthesis

116176-92-2
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773-91-1
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Yield: 77%

Reaction Conditions:

with tert.-butylhydroperoxide;copper diacetate in water;acetonitrile at 50; for 12 h;Catalytic behavior;

Steps:

General Procedure for the Oxidation Reaction
General procedure: Cu(OAc)₂(0.025 mmol), indoles (0.5 mmol), TBHP (1 mL, 70 % solution in water) and CH₃CN (3.0 mL) were added to glass tube via syringe. The reaction mixture was stirred at 50°C for 12 h. It was then quenched (consumption of residual TBHP) with saturated Na₂SO₃ solution and extracted with EtOAc. The organic layer was combined and dried with Na₂SO₄. Removal of solvent followed by flash column chromatographic purification (Ethyl acetate/Petroleum ether=5/1) afforded products.

References:

Luo, Junfei;Zhao, Yanchao;Xu, Xing;Zheng, Junliang;Liang, Hongze [Tetrahedron Letters,2017,vol. 58,# 49,p. 4591 - 4594] Location in patent:supporting information