Boron tribromide → HCID 54206997, compound

Participants

Reaction Steps

To a solution of 2.50 g (13.0 mmol) 2,6-diethyl-4-methoxy-benzaldehyde in 15 ml dichloromethane at −60° C. was added dropwise 26.0 ml (26.0 mmol) of a 1 M solution of boron tribromide in dichloromethane. After the addition was complete, the reaction mixture was allowed to warm to room temperature and then heated at reflux for 16 h. The reaction mixture was then cooled to room temperature and poured onto an ice-water mixture. The mixture was diluted with dichloromethane, the phases were separated, and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was resuspended in a 1:1 mixture of ethyl acetate and diethyl ether and extracted with 1 N aqueous sodium hydroxide solution. The phases were separated and the aqueous phase was acidified to pH 1 by addition of concentrated hydrochloric acid and then extracted with ethyl acetate. The phases were separated and the organic phase was washed with saturated brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 1.48 g (64%) of the title compound as a brown crystalline solid. MS (ISP): 177.4 ([M−H]−).

Provenance & Evidence