Ethyl 2,2-dibromoacetate

Ethyl dibromoacetate [105-36-2] M 245.9, b 81-82°/14.5mm, n22 1.4973. Washed briefly with cone aqueous NaHCC>3, then with aqueous CaCl2. Dried with CaS04 and distd under reduced pressure. 

More recently, Concellon has reported a stereoselective method for the formation of ( )-a,p-unsaturated esters that exploits a Sml2 Reformatsky reaction followed by an elimination.141 For example, ethyl dibromoacetate reacts with benzaldehyde in the presence of Sml2 to form samarium alkoxide 126, which is reduced further to give a second Sm(III) enolate 127. Elimination then affords ( )-a,p-unsaturated ester 128 in good yield (Scheme 5.90).141... 

Ethyl crotonate, 100 Ethyl cyclobutanecarboxylate, 381 a-Ethylcyclohexanone, 343 Ethyl diazoacetate, 109, 110, 193-194, 464 Ethyl dibromoacetate, 19S Ethyl dichloroacetate, 195 N-Ethyl-5,7-dichlorobenzisoxazolium fluoroborate, 192... 

Reaction with organoboranes.1 Brown has extended the reaction of ethyl bromo-acetate with trialkylboranes to ethyl dibromoacetate. If one equivalent of potassium r-butoxide is used, an a-halocarboxylic acid is obtained dialkylation is achieved by use of two equivalents of the base. Since the first reaction occurs readily at 0°, whereas the second requires a higher temperature (50°), two different alkyl groups... 

Esters from olefins Ethyl bromoacetate. Ethyl dibromoacetate. 

THF at 0°. This is immediately followed by dropwise addition of methanesulfonic acid. The B-phenyl-9-BBN (2) is obtained in 85% yield. This product (2) is then allowed to react with ethyl bromoacetate (2, 192-193), ethyl dibromoacetate (2, 195), and various bromoketones as described previously to give a-aryl derivatives such as (3).10... 

Ethylcyclohexene, 209 Ethyl diazoacetate, 137, 138—139, 210 Ethyl dibromoacetate, 26, 28, 236 Ethyl dichloroacetate, 26 Ethyl tram,cis,irans-3,1 l-dimethyl-7-ethyl-trideca-2,6,10-trienoate, 110 Ethyl diphenylphosphonite, 139—140 Ethylene chlorohydrin, 272 Ethylenediamine, 57 Ethylene dibromide, 159 Ethylene glycol, 274 Ethyleneketals, 140 Ethylene oxide, 140 Ethyl farnesoate, 110 Ethyl 3-hexenoate, 236 Ethyl 3-hydroxybutanoate, 310 Ethyl 3-hydroxy-3-methylbutyrate, 118 9-Ethylidenefluorene, 35 Ethylidene iodide, 141... 

Compounds (36) may be formed in Reformatsky reactions between ethyl dibromoacetate or ethyl trichloroacetate and the appropriate diethyl alkyl-idenemalonates. In these reactions also, there is an intramolecular displacement of a halide by a carbanionic residue. 

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