Dibromomethane → HCID 86737969, compound

Participants

Reaction Steps

A solution of 44 g (0.104 mole) of 6-chloro-7,8-dihydroxy-1-(p-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide in 700 ml of dry dimethylformamide was treated with 45.5 g (0.784 mole) of potassium fluoride. After five minutes, 11.2 ml (27.6 g, 0.109 mole) of dibromomethane was added. The mixture was heated at 115° and held at 115° for 6 hours. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate and washed several times with water. The dried, concentrated product was chromatographed over 800 g of silica gel with a 1 to 3% methanol in chloroform gradient. The homogeneous fractions gave 30.4 g (71%) of 6-chloro-7,8-methylenedioxy-1-(p-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide. A sample was crystallized from acetonitrile to give white crystals, m.p. 191°-193°.

Provenance & Evidence