Boron tribromide → HCID 70506781, compound

Participants

Reaction Steps

To a solution of 1-(N,N-diphenylaminomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (0.38 g) in anhydrous dichloromethane (15 ml) was dropwise added a solution of boron tribromide (0.75 g) in anhydrous dichloromethane (5 ml) at -60° C. with stirring. The mixture was stirred for 2.5 hours at the same temperature and the reaction temperature was elevated to ambient temperature over 19 hours. Dichloromethane was removed and to the residue were added methanol and a small amount of water. The mixture was warmed and concentrated to dryness. The residue was crystallized with a mixture of acetone and ether and the crystals were collected by filtration to give 1-(N,N-diphenylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (0.33 g).

Provenance & Evidence