1,2-Dibromoethane → HCID 53685959, compound

Participants

Reaction Steps

To a mixture of the above oxime (5.0 g, 20 mmol), 1,2-dibromoethane (18 ml) and N,N,N,N-tetrabutylammonium bromide (0.61 g, 3 mmol) was carefully added 12N sodium hydroxide (19 ml) while the temperature was kept below 35° C. After stirring at ambient temperature for 17 h, water (50 ml) was added and the resulting mixture was extracted with dichloromethane (2×100 ml). Water (100 ml) was added to the combined organic phases and pH in the aqueous phase was adjusted to 5 with 10% citric acid. The organic phase was washed with water (50 ml) and brine (10 ml) and dried (MgSO4). The solvent was evaporated in vacuo and the residue purified by column chromatography on silica gel (100 g, gradient n-heptane to n-heptane/ethyl acetate 20/1) to give 4.7 g of 1,2-bis(4-fluorophenyl)ethanone O-(2-bromoethyl)oxime.

Provenance & Evidence