Bromination of alcohols by boron tribromide

Manganese/bipyridine-catalyzed non-directed C(sp3)–H bromination using NBS and TMSN3

“…Organic halides are versatile precursors for various synthetic protocols and are frequently used to introduce a variety of functionalities, such as boron-, silicon-, nitrogen-, and oxygen-based functional groups, and in C−C bond forming reactions, such as cross-coupling reactions [1][2][3][4][5][6]. The traditional method used for the preparation of alkyl bromides is the reaction of their corresponding alkyl alcohols with HBr, PBr 3 , or other brominating reagents [7][8][9][10][11][12][13].…”

Synthesis of Unsaturated Drying Oils from Saturated Fatty Oils Derived from Renewable Feedstocks

“…In principle, if saturated oils can be halogenated and subsequently dehydrohalogenated, unsaturation can be created in the molecule. To our knowledge, there are no reports on such a protocol for functionalization of saturated lipids in any of the prior work, even though there are reports on functionalization of partially saturated oils and saturated alkanes. − We considered it as a desirable objectiveboth from the viewpoint of sustainability and use of more diverse and affordable feedstocks for alkyd preparation.…”

Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes

“…41 The hydroxyl groups in the substrates were converted into bromides simultaneously by the action of BBr 3 to give a series of useful dibromides. 42 We were interested in whether alcohol-containing substrates can be hydrobrominated in the absence of an external proton source. To our delight, 1t was able to undergo anti-Markovnikov hydrobromination to give 2t with only a slight drop in yield (76%), and 2u was produced in quantitative yield.…”