Epibromohydrin

A mixture of 1.63 g of 5-hydroxy-3,4-dihydrocarbostyril, 2.5 g of epibromohydrin and 2 drops of piperidine was heated at a temperature of 95°C to 100°C for a period of 4 hours with stirring. The reaction mixture was then concentrated to dryness under reduced pressure and the residue was recrystallized from acetone to obtain 1.2 g of 5-(2,3-epoxy)propoxy-3,4-dihy-drocarbostyril as a colorless powder having a melting point of 172°C to 173°C,... 

Endomethylene-A -tetrahydro benzaldehyde Cyclothiazide Epibromohydrin Carteolol Epichlorohydrin Acebutolol Atenolol Befunolol Betaxolol HCI Bufetrol Bunitrolol Bupranolol Carazolol Carnitine Celiprolol Colestipol Cromolyn sodium I ndenolol Mazindol Mepindolol Metoprolol tartrate Nadolol Nifuratel Oxprenolol Penbutolol Practolol Propafenone HCI Propranolol HCI Viloxazine HCI Xanthinol niacinate Epinephrine... 

Figure 2. Conversion versus time for substitution by tetrabutyl-ammonium benzoate on poly(epibromohydrin) (O) poly[(2-bromo-ethyl )oxirane] (0) poly[(3-bromopropyl )oxirane] (v, , separate runs) and poly [(4-bromo butyl )oxirane] (a, , separate runs).

Langer and coworkers have utilized dianions of 3-ketoesters or 1,3-diketones 2-220 with epibromohydrin (2-222) in SN/SN domino processes to give functionalized 2-alkylidene-5-hydroxymethyltetrahydrofurans 2-222 (Scheme 2.52) [127]. 

Add 200 mg of sodium carbonate per ml of the dendrimer solution prepared in step 1 and a quantity of epibromohydrin equal to a 285-fold molar excess over the amount of... 

Figure 7.18 Amine-containing dendrimers can be activated with epibromohydrin to result in the formation of reactive epoxy groups on the dendrimer surface. This reactive intermediate then can be used to conjugate with thiol-containing proteins, such as thiolated alkaline phosphatase. The reaction results in the formation of a thioether bond.

Eicosene, i2 Elaidic acid, oil Enanthic alcohol, hll Enanthylic acid, h9 Epibromohydrin, b328 Epichlorohydrine, cl20 1,4-Epoxybutane, t69... 

Epoxides (e.g., with acid present) Butylene oxide, ethylene oxide, diepoxy butane, epibromohydrin... 

The same immobilized catalyst 36 [69] was also effectively used for dynamie hydrolytic kinetic resolution of epibromohydrin. Five reaction cycles performed with single eatalyst bateh provided combined yield of 94% with 96% ee and in 90% ehemieal purity for the product l-bromo-2,3-propandiol (Scheme 14). 

Scheme 14. Dynamic kinetic resolution of epibromohydrin with polymer bound catalyst 36.

Scheme 18. A possible application of the enantioselective ring opening of epibromohydrin with phenols in combinatorial synthesis using the catalyst 36...

Dilithiated hydrazones of methyl ketones 266 can be transformed into 1,2,3,4-tetrahydropyridazines 268 upon reaction with epibromohydrin 267 (Equation 66) <2006JOC2293>. 

Double deprotonation/alkylation of (/ )-4-phenyl-3-oxazolidineacetonitrile with LDA/HMPA and epibromohydrin or triflylmethyloxirane afforded the cyclopropyl derivative with a diastereomeric ratio of 44 37 12 7, which was independent of the reaction conditions and the nature of the electrophile70. Since separation of the main isomers by flash chromatography (silica gel, ethyl acetate/hexane 40 60) was possible, optically pure 1 -aminocyclopropanecarb-oxylic acids (methanohomoserines) were obtained after further transformations. 

An interesting attempt to prepare a perchlorate polymer was made by Radell and Connolly [11]. They prepared epiperchloratohydrin (I) from epibromohydrin ... 

The early literature of epoxide chemistry contains several accounts of the reaction of hydrogen cyanide with epichlorohydrin, 11-1T1 epibromohydrin,10 ethyl glycidyl ether,J- and related substance Attack by the nucleophilic aperies, CN- ion in this case, occurs uniquely at the site furthest from the polar atom,. e. at the terminal epoxidi-carbon atom (Eq. 787), An important contribution was made by... 

A related oxidation is that employed by Richter14 and later by Fischer and Leuohs 4 and also by Abderhalden and ISchvtld.1 to convert epichlorohvdrin and epibromohydrin into the corresponding hydroxy acids (Eq. 427). 

A salen-cobalt complex has been appended to the PASSflow monolith system to form catalyst 42 and used for the dynamic kinetic resolution of epibromohydrin, 43. Because 43 undergoes rapid racemization under the conditions used, all the starting materials can theoretically be converted to the desired diol 44 (Scheme 4.75). The... 

A mixture consisting of the Step 1 product (1.87 mmol), epibromohydrin (2.06 mmol), K2C03 (3.7 mmol), and 2 ml DMF was heated 2 hours at 60°C in a sealed vial. The mixture was then partitioned between EtOAc/water and the organic phase washed twice with water and once with brine. The solution was concentrated, the solid residue purified by chromatography on silica gel, and the product isolated in 44% yield as a white solid. 

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