2004
DOI: 10.1039/b315340a
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A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate

Abstract: Cyclic ketones reacted with N-bromosuccinimide (NBS) catalysed by NH(4)OAc in Et(2)O at 25 degrees C to give the corresponding alpha-brominated ketones in good yields, while acyclic ketones were efficiently brominated in CCl(4) at 80 degrees C.

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Cited by 146 publications
(61 citation statements)
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“…19 Initially, the 2-bromo-1-(substituted phenyl)ketones 1a-k were reacted with sodium azide in an attempt to synthesize the corresponding 2-azido-1-(substituted phenyl)ketones. However, the isolation of the corresponding 2-azido-1-(substituted phenyl)ketones was in poor yields.…”
Section: Resultsmentioning
confidence: 99%
“…19 Initially, the 2-bromo-1-(substituted phenyl)ketones 1a-k were reacted with sodium azide in an attempt to synthesize the corresponding 2-azido-1-(substituted phenyl)ketones. However, the isolation of the corresponding 2-azido-1-(substituted phenyl)ketones was in poor yields.…”
Section: Resultsmentioning
confidence: 99%
“…7 We studied the bromination of ketone 4 under various conditions. Aromatic methyl ketones can be brominated with molecular bromine in organic solvents, 9,10 cupric bromide, 11 ammonium perbromides, 12 N bromosuccin imide, 13 and some other reagents. Bromination of ketone 4 with molecular bromine in acetic acid and CH 2 Cl 2 was ineffective.…”
Section: Methodsmentioning
confidence: 99%
“…The synthesis involved the use of the previously reported 2-[4-bromo-2-(N,Ndimethylamino)phenyl]ethanol. 24,25 200 mg (0.82 mmol) of bromide was dissolved under argon atmosphere in 8 ml of dry THF. The solution was cooled down to -78 ºC, and then 1.23 ml (1.97 mmol) of a 1.6 M butyl lithium solution was added dropwise.…”
Section: Synthesis Of Cations 1 Andmentioning
confidence: 99%