Boron tribromide → HCID 22413374, compound

Participants

Reaction Conditions

Reaction Steps

1.10 g (0.0033 mol) 1 -(benzofuran-7-yl)-6,7-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1-H-3-benzazepine was dissolved in 25 ml dry dichloromethane. The solution was cooled to -60° C. and 0.93 (0.0098 mol) boron tribromide was slowly added. The reaction mixture was stirred at -60° C. for 15 min., allowed to warm up to 0° C. and stirred for 1 h. Evaporation in vacuo left a brown residue, which was redissolved in dichloromethane. The solution was stirred in an ice bath and 5 ml methanol was added dropwise. The solution was again concentrated in vacuo, the residue was dissolved in 6N HCl and refluxed for 30 min. Then pH was adjusted to 8 with 2N NaOH-solution and the product extracted with ethylacetate. The organic layer was washed with water and brine and concentrated in vacuo. 1-(Benzofuran-7-yl)-6,7-dihydroxy-3-methyl-2,3,4,5,-tetrahydro-1H-3-benzazepine was obtained as an offwhite powder.

Provenance & Evidence