3-Nitrobenzaldehyde → HCID 22000958, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromoaniline (1.72 g, 10 mmol), 2-methyl-3-butyn-2-ol (1.1 g, 13 mmol), 3-nitrobenzaldehyde (0.5 g, 3.3 mmol), triethylamine (5 g), dichlorobis(triphenyl-phosphine)palladium (15 mg) and triphenylphosphine (80 mg) was deaerated by bubbling nitrogen. The reaction mixture was heated to 80° C. and treated with CuI (10 mg). After 7 hr at reflux thin-layer chromatography showed nearly complete conversion of the 3-bromoaniline to a mixture of 3-aminophenylacetylene dimethylcarbinol and N-(3-nitrobenzylidene) aminophenyl acetylene dimethylcarbinol.

Provenance & Evidence