Oxidative bromination of ketones using ammonium bromide and oxone®

A New Synthetic Approach to Prostaglandin Analogues: Synthesis of Bimatoprost via Lipase Enzymatic Catalysis

“…Further, we have developed an alternative synthetic route for the synthesis of compound 7, from an iodo derivative of 4-phenylbutan-2-one (5) with an improved yield. In the alternative route, 4-phenylbutan-2-one (5) was treated with cupric oxide/iodine in methanol and methylene chloride mixture at 42 ºC for 15 h to obtain an iodo-intermediate (8). This intermediate was further treated with trimethyl phosphite to obtain compound 7 in good yield.…”

“…Bimatoprost (4) is a synthetic prostaglandin used topically for the reduction of elevated intraocular pressure (IOP) in patients with open angle glaucoma or ocular hypertension [7]. α-Bromoketones [8,9] and α-iodoketones [10] are the most promising intermediates in the organic synthesis due to their high reactivity to react with a variety of nucleophiles to result useful biological active compounds. An alternative method was developed to prepare organophosphorus ylides from α-bromoketone and α-iodoketone under mild conditions.…”

Managing Hazardous Reactions and Compounds in Process Chemistry

“…The method allows for the monobromination of arylalkyl, cyclic, acyclic 1,3-diketones and β-keto esters. α,α-Dibromination can be achieved by use of more reagents (159). Other brominating reagents have found widespread usage in batch chemistry rather than flow, such as N-bromosuccinimide (NBS).…”

Efficient and convenient epoxidation of alkenes to epoxides with H2O2 catalyzed by Co(OAc)2 in ionic liquid [C12py][PF6]

“…[3][4][5], and suffer from considerable drawbacks such as low yield, harsh or delicate reaction condition, and a large amount of waste byproducts. Oxidation with NaClO [6,7], PAA [8], TBHP [9,10], PhIO [11,12], NaIO 4 [13,14], CHP [15], oxone [16][17][18], peracetic acid [19,20], TADOOH [21], PPO [22], and other reagents [23][24][25][26][27][28] have also been developed for this conversion. However, these protocols are generally associated with one or more disadvantages, such as complex handling procedures, problematic side reactions, the use of expensive, toxic and moisture-sensitive reagents, long reaction times, low yields, and environmental concerns associated with the use of poorly manageable catalysts.…”