Synthesis of alkyl bromides

Name Reactions

Recent Literature

Nucleophilic fluorination using CsF or alkali metal fluorides was completed in short reaction time in the presence of [bmim][BF₄] affording the desired products without any byproducts. Facile nucleophilic substitutions such as halogenations, acetoxylation, nitrilation, and alkoxylations in the presence of ionic liquids provided the desired products in good yields.
D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2003, 68, 4281-4285.

Silicaphosphine (Silphos), [P(Cl)₃−n(SiO₂)n] is a new heterogeneous reagent that converts alcohols and thiols to their corresponding bromides and iodides in the presence of molecular halogen in refluxing CH₃CN in high to quantitative yields. Separation of the Silphos oxide byproduct can be achieved by a simple filtration.
N. Iranpoor, H. Firouzabadi, A. Jamalian, F. Kazemi, Tetrahedron, 2005, 61, 5699-5704.

The preparation of alkenyl halides of any length from inexpensive starting reagents is reported. Standard organic transformations were used to prepare straight-chain α-olefin halides in excellent overall yields with no detectable olefin isomerization and full recovery of any unreacted starting material.
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.

An efficient conversion of alcohols and β-amino alcohols to the corresponding chlorides can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro[1,3,5]triazine and N,N-dimethyl formamide. Addition of NaBr allows the synthesis of bromides. Optically active carbinols react under inversion.
L. de Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 2002, 4, 553-555.

Sm(OTf)₃ is an effective catalysts for a versatile and efficient halogen-promoted highly regio- and stereoselective Friedel-Crafts (F-C) alkylation of electron-rich arenes with alkenes and α,β-unsaturated carbonyl compounds in the presence of NBS or I₂ as halogen sources.
S. Haira, B. Maji, S. Bar, Org. Lett., 2007, 9, 2783-2786.

C. Ye, J. M. Shreeve, J. Org. Chem., 2004, 69, 8561-8563.

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.