One-pot synthesis of α-bromoacetals of ketones from secondary alcohols and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in ethylene glycol

ABSTRACT

α-Bromoacetals of ketones were prepared from various secondary alcohols with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and ethylene glycol through oxidation, bromination, and acetalization in one pot without the use of other catalysts under mild conditions. The effects of DBDMH, the solvent, and N-bromosuccinimide on the reaction were investigated. Under the optimal conditions, most α-bromoacetals of ketones were obtain in 90–98% yields.

GRAPHICAL ABSTRACT

KEYWORDS:

• 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH)
• α-bromoacetals of ketones
• one pot
• oxybromoacetalization
• secondary alcohol

Additional information

Funding

The authors thank the Education Department of the Anhui Province for financial support (No. KJ2016A684, KJHS2017B13).