Bromobenzene → HCID 70568455, compound

Participants

Reaction Steps

To a solution of 3,14-dimethoxy-[α,17-dimethyl-4-hydroxymorphinan-6-one (21) (0.4 g, 1.159 mmol) in dry pyridine (1 ml) was added bromobenzene (0.205 g, 1.35 mmol) and 0.216 g (1.565 mmol) of K2CO3 (freshly dried at 110° C. for 2 hours in a vacuum oven and quickly ground and sieved to 200 mesh). More pyridine (0.5 ml) followed by copper powder (20 mg, 10 micron) was added and the mixture was refluxed (oil bath temperature 130°-140°) for 24 hours under a nitrogen atmosphere with stirring. The mixture was filtered while hot and the residue was washed with hot pyridine (2 ml). After adding 10 ml of toluene, the solution was concentrated under reduced pressure to give (22) as a foamy solid. Thin layer chromatography on a silica gel plate (solvent system: CHCl3 :MeOH, 80:20) showed a single spot. The compound was quickly chromatographed on a silica gel column and eluted with graded methanol/chloroform mixtures to give 0.45 g (92% theory) of 3,14-dimethoxy-8α,17-dimethyl-4-phenoxymorphinan-6-one (22) as a foamy solid.

Provenance & Evidence