Citation: MAI Wenpeng, YANG Liu, LYU Mingxiu, WANG Yanwei, CAO Yi, LU Kui. Metal-Free Synthesis of 3,3-Difluoro-2-Oxindoles[J]. Chinese Journal of Applied Chemistry, ;2016, 33(11): 1279-1283. doi: 10.11944/j.issn.1000-0518.2016.11.160035 shu

Metal-Free Synthesis of 3,3-Difluoro-2-Oxindoles

1.
School of Materials and Chemical Engineering, He'nan Institute of Engineering, Zhengzhou 450006, China

Corresponding author: MAI Wenpeng, LU Kui,
Received Date: 21 January 2016
Available Online: 7 April 2016
Fund Project:

A novel method for the synthesis of 3,3-difluoro-2-oxindoles was developed. 2-Bromo-2,2-difluoro-N-phenylacetamide was prepared from neat simple aromatic amines with ethyl bromodifluoroacetate. Reflux of the product in CH₃CN with CH₃I for 24 h gave 2-bromo-2,2-difluoro-N-methyl-N-phenylacetamide in 75%~90% yields. In the presence of 3.0 chemometric number sodium formaldehyde sulfoxylate, this key intermediate undergoes intramolecular radical cyclization in aqueous solution(N,N-dimethylformamide/H₂O) and affords the final product 3,3-difluoro-1-methylindolin-2-ones in 53%~72% yields. This method can be performed in aqueous solution from commercially available and affordable starting materials without any metal catalysts. It shows potential in industrial production of 3,3-difluoro-2-oxindoles.
- acetanilide,
- sodium formaldehyde sulfoxylate,
- difluoro-methylindolin-one,
- metal-free
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沈阳化工大学材料科学与工程学院沈阳 110142