Categories: C-Br Bond Formation >
Synthesis of 1,2-dibromoalkanes
Recent Literature

Bromination of alkenes, alkynes, and anilines has efficiently been carried out
at room temperature in short reaction times using potassium bromide and
orthoperiodic acid in dichloromethane-water (1:1) to prepare the corresponding
brominated compounds with excellent yields.
A. Khazaei, M. A. Zolfigol, E. Kolvari, N. Koukabia, H. Soltania, F. Komakia, Synthesis, 2009,
3672-3676.

In bromination of alkenes by dibromine and dealkylation of aromatic ethers
by boron tribromide, a fluorous phase acts as a liquid membrane permitting
passive transport of the reagents at the bottom to the top layer involving
the substrates, thereby regulating the reactions.
I. Ryu, H. Matsubara, S. Yasuda, H. Nakamura, D. P. Curran, J. Am. Chem. Soc., 2002,
124, 12946-12947.

Unsaturated compounds such as alkenes, alkynes, allenes, and
methylenecyclopropanes (MCPs) can be dibrominated within minutes by NBS and
lithium bromide in THF at room temperature in good to excellent yields under
mild conditions.
L.-X. Shao, M. Shi, Synlett,
2006, 1269-1271.

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.

An efficient method allows the construction of 2,6-cis-4,5-dibromo-tetrasubstituted
tetrahydropyran rings with well-controlled stereochemistry in good yields.
F. Liu, T.-P. Loh, Org. Lett., 2007,
9, 2063-2066.
