Citation: Qi Zhong Zhou, Chun Lin He, Zhen Chu Chen. Cyclization and halogenation of substituted o-allylphenols with diacetoxyiodobenzene in the presence of iodine or bromine[J]. Chinese Chemical Letters, ;2008, 19(6): 661-664. doi: 10.1016/j.cclet.2008.04.003 shu

Cyclization and halogenation of substituted o-allylphenols with diacetoxyiodobenzene in the presence of iodine or bromine

Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Received Date: 1 December 2007

Fund Project: We thank the National Science Foundation of China for financial support (No. 29472036).

Substituted 2-halomethy1-2,3-dihydrobenzofurans were synthesized in one pot and in mild yield from substituted o-allylphenols with diacetoxyiodobenzene in the presence of I₂ or Br₂in dry CH₂Cl₂ under reflux.
- 2-Halomethy1-2,3-dihydrobecnzofuran,
- Diacetoxyiodobenzene,
- Cyclization,
- Halogenation
1. [1]
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