1970-56-5

Upstream product

• 20769-85-1 2-bromoisobutyric acid bromide 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 128966-11-0 3-(4-Methoxyphenyl)-5,5-dimethyl-2-dimethylaminooxazolidin-4-one 
• 35844-02-1 p-methoxy-α-nitroisobutyranilide 
• 7274-71-7 N-(4-methoxyphenyl)-2-methylacrylamide 
• 85576-95-0 N-(4-Methoxy-phenyl)-N-[1-(4-methoxy-phenylcarbamoyl)-1-methyl-ethyl]-2-methyl-acrylamide 

Relevant academic research and scientific papers

Bromo-nitro substitution on a tertiary α carbon - A previously uncharacterized facet of the Kornblum substitution

Sodium nitrite in dimethylformamide substitutes nitro for bromine alpha to an amide carbonyl in high yield at a tertiary site. Hammett plots show a strongly positive ρ value (+0.67), indicating a negatively-charged transition state, in contrast to the typical SN1/SN2 mechanism domain for Kornblum substitutions. 2015

The Conversion of Phenols to Primary and Secondary Aromatic Amines via a Smiles Rearrangement

The conversion of phenols to 2-aryloxy-2-methylpropanamides (1) and the Smiles rearrangement of these to N-aryl-2-hydroxy-2-methyl propanamides are described; hydrolysis of the latter compounds yields anilines.The scope and limitations of reaction are discussed.Routes, some involving α-lactams, from phenols to N-substituted derivatives of (1) have been developed.Under the conditions of the Smiles rearrangement these secondary 2-methylpropanamides can form directly anilides, N-alkylanilines, or benzoxazinones.