Premium
Monobromination of α , ω ‐Diols: Highly Efficient Preparation of Synthetic Intermediates
Author(s) -
Oliveira Adeildo Junior,
Souza Isis Torres,
Bernardo Vanderson Barbosa,
Santos Larissa C.,
Lima Maria Raquel Ferreira,
Goulart Henrique Fonseca,
Goulart Santana Antônio Euzébio
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901879
Subject(s) - toluene , dichloroethane , chemistry , solvent , molar ratio , organic chemistry , 1,2 dichloroethane , medicinal chemistry , catalysis
The present work aimed to evaluate different conditions to perform monobromination reactions of α , ω ‐diols using HBr. Three solvents were tested, toluene, isooctane, 1,2‐dichloroethane, in two distinct molar proportions between 1,8‐octanediol and HBr (1:1 and 1:2 equivalents). All reactions occurred under reflux. After stablishing the best reactional conditions, assays with four symmetric α , ω ‐diols, 1,6‐hexanediol; 1,7‐heptanediol; 1,8‐octanediol; and 1,10‐decanediol, with 2 eq. HBr in 1,2‐dichloroethane, were conducted. Using toluene as solvent lead to the best reaction yields (81‐95%), producing the least amount of unwanted dibrominated product. Reactions in 1,2‐dichloroethane gave similar results to the ones with toluene when 2 eq. HBr were used. The lowest reactional efficiency registered in these assays occurred in isooctane, forming the highest amount of dibromide. Diols 1,7‐heptanediol and 1,8‐octanediol showed the best results under the conditions studied, in 1,2‐dichloroethane.