Hydroxyamine hydrochloride → 7-Bromo-9,9-diethylfluorene-2-carbonitrile

Participants

Reaction Steps

An alternate, but less satisfactory synthesis was conducted as follows: A mixture of 7-bromo-9,9-diethylfluorene-2-carboxaldehyde (3.29 g, 10.0 mmol), hydroxylamine hydrochloride (0.9 g, 10.0 mmol), and formic acid (15 mL), was held at reflux for 2 hours, cooled and filtered. The filtrate was worked up by extraction into toluene, washing the extract with water, and bicarbonate solution, drying and concentration. The residue was combined with the formic acid-insoluble solids, and chromatographed over silica gel. There were obtained, the desired nitrile product, 1.58 g (49%), m.p. 85-87° C., mass spectrum (m/z): 325, 327 (M+); the amide byproduct, 0.42 g (12%), m.p. 179-184° C., mass spectrum (m/z): 343, 345 (M+); and the oxime by-product, m.p. 104-107° C., 0.17 g (5%), mass spectrum (m/z): 343 (M+)

Provenance & Evidence