1,2-Dibromoethane → 3-methylbutyrophenone O-(2-bromoethyl)oxime

Participants

Reaction Conditions

Reaction Steps

A mixture of the above oxime (5.0 g, 28 mmol), 1,2-dibromoethane (25 ml) and N,N,N,N-tetrabutylammoniumbromide (1.0 g, 3 mmol) was cooled to 0° C. and 9N sodium hydroxide (35 ml) was carefully added. The mixture was stirred vigorously at room temperature for 3 days. Water (50 ml) was added and the resulting mixture extracted with dichloromethane (2×100 ml). To the combined organic phases was added water (50 ml) and pH in the aqueous phase was adjusted to 5 with 10% aqueous citric acid. The organic phase was washed with water (50 ml) and brine (50 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 8.0 g of 3-methylbutyrophenone O-(2-bromoethyl)oxime.

Provenance & Evidence