N-Bromoacetamide as reagent

Bromine, reaction with phenylacetylene and sodium hydroxide to give phenylbromoethyne, 46, 86 N-Bromoacetamide, as reagent for bromofluorination of 1-heptene, 46,10... 

Bromine trifluoride 17, 626 N-Bromoacetamide as reagent 16, 942 17,590 1,2-Bromofluorides (s. a. 5a-Bromo-6y5-fluorosteroids)... 

In contrast with the behaviour of typical vinylphosphonic acid derivatives, the carbon-carbon double bond in the 1,2-oxa-phospholene (167) is remarkably unreactive towards a broad spectrum of reagents including electrophiles, most epoxidizing and organometallic reagents, as well as to dipolar addition reactants. Exceptional reagents are, however, N-bromoacetamide (NBA), ozone, dimethyllithiumcuprate, and sodium-naphthalene. 

Notes Used for allylic and benzylic brominations (Wohl-Zieeler Reaction). With moist DMSO the reagent is useful for bromohydrin formation, providing trans addition of bromine and water. Can brominate alpha to carbonyl in carbonyl (carboxyl)-containing compounds. With DMF useful for aromatic bromination of activated aromatic rings, such as phenols, aromatic ethers, aniline derivatives and activated heterocyclic compounds. For similar chemistry, see also NBA, N-Bromoacetamide. 

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