Categories: C-Br Bond Formation >
Synthesis of bromohydrins
Recent Literature
Highly regioselective ring opening of epoxides to halohydrins has been
carried out in impressive yields with hydrogen and lithium halides in presence
of β-cyclodextrin using water as solvent.
M. Arjun Reddy, K. Surendra, N. Bhanumathi, K. Rama Rao, Tetrahedron,
2002, 58, 6003-6008.
A very rapid and efficient method has been developed for the synthesis of
vicinal bromohydrins and alkoxybromides directly from olefins without any
catalyst using N,N-dibromo-p-toluenesulfonamide (TsNBr2)
as the brominating agent in CH3CN-water or alcohol.
P. Phukan, P. Chakraborty, D. Kataki, J. Org. Chem., 2006,
71, 7533-7537.
P. Phukan, P. Chakraborty, D. Kataki, J. Org. Chem., 2006,
71, 7533-7537.
The reaction of tribromoisocyanuric acid with alkenes in the presence of
nucleophilic solvents (various alcohols, acetic acid, and H2O in
acetone) led to the corresponding β-bromoethers, β-bromoacetates and
bromohydrins in high regioselectivity and good yields.
L. S. de Almeida, P. M. Esteves, M. C. S. de Mattos, Synlett,
2006, 1515-1518.
Oxidative
bromination of different types of olefins using Selectfluor/KBr afforded addition,
monobromo-substituted, or Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem.,
2004,
69, 8561-8563.
