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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 12
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Original Articles

Dibromomethane as One‐Carbon Source in Organic Synthesis: The Mannich Base Formation from the Reaction of Phenolic Compounds with a Preheated Mixture of Dibromomethane and Diethylamine

, &
Pages 2253-2267 | Received 15 Dec 2003, Published online: 17 Aug 2006
 

Abstract

The salt formed from the reaction of dihalomomethane and diethylamine reacted with phenolic compounds to give the corresponding Mannich bases in modest to good yields. As for the relative rates and yields are in the following order: CH2Br2 > CH2Cl2. The CD2Cl2 is also applicable to prepare the deuterated analogues. At higher temperature, the elimination of diethylamine from Mannich base occurred to give the corresponding o‐quinone methide intermediate, which was then trapped by another phenolic compound to give bis(2‐hydroxy‐1‐aryl)methanes.

Acknowledgments

We are grateful to the National Science Council, National Chung Cheng University, and Academia Sinica, Republic of China for financial support.

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