Synthesis of 1-Bromo-3-butyn-2-one and 1,3-Dibromo-3-buten-2-one

Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-v...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2009-06, Vol.39 (14), p.2472-2480
Main Authors: Mekonnen, Alemayehu, Westerlund, Andreas, Havelkova, Martina, Descomps, Alexandre, Carlson, Rolf
Format: Article
Language:English
Subjects:
2-bromomethyl-2-vinyl-1,3-dioxolane
Acetal deprotection
bromination
dehydrobromination
formolysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-vinyl-1,3-dioxolane is converted to 2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane. Double dehydrobromination with t BuOK affords 2-ethynyl-2-bromomethyl-1,3-dioxolane. Formolysis with formic acid gives 1-bromo-3-butyn-2-one. Deacetalized 2-bromoethyl-2-vinyl-1,3-dioxolane was treated with Br 2 and Li 2 CO 3 /12-crown-4 in tetrahydrofuran to give 1,3-dibrom-3-buten-2-one in moderate yield.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910802654872