Cyanogen Bromide → cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

Participants

Reaction Steps

0.45 g (1.92 mmol) of 8-fluoro-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one was dissolved in 6 ml of anhydrous chloroform and added dropwise at room temperature over 15 minutes to a solution of 244 mg (2.3 mmol) of cyanogen bromide in 2 ml of anhydrous chloroform. Subsequently, the mixture was heated under reflux for a further 75 minutes, concentrated in a vacuum, taken up with 12 ml of 2N hydrochloric acid and heated under reflux over 6 hours. Subsequently, the mixture was made basic with 3N sodium hydroxide solution and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed once with 70 ml of saturated sodium chloride solution, dried (MgSO4) and concentrated in a vacuum. 0.29 g (69%) of cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one was obtained as a yellow oil.

Provenance & Evidence