Dichloromethane → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

150 ml of CH2Cl2, 25 g of (I) and 21 g of N-bromosuccinimide are loaded under nitrogen in a 500 ml pyrex round-bottom flask, and irradiated from the outside with a 300 watt halogen lamp, refluxing for 2 hours. 150 ml of water are added. 80 ml of CH2Cl2 are distilled off, 150 ml of toluene and 5 g of PEG 6000 are added while distilling off CH2Cl2 at inner temperature of 85-90° C. The mixture is left for 3 hours at said temperature, water is removed at 60° C., the mixture is washed with 2×50 ml of water and 30-40 ml of toluene are distilled off at 40 mm/Hg. The mixture is cooled at 0° C. for 2-3 hours, filtered, washed with 20 ml of toluene at 0° C. and air-dried at 60° C., to obtain 20.4 g of (VI) m.p. 110-111° C., with good purity. From mother liquors a further 1.8 g are recovered (overall yield 82%).

Provenance & Evidence