Bromobenzene → HCID 70552443, compound

Participants

Reaction Steps

Compound 2 (18.80 g, 42 mmol) was dried by azeotropic distillation several times with pyridine and then dissolved in pyridine (100 ml). To this solution was added bromobenzene (4.90 ml, 46 mmol), powdered potassium carbonate (6.40 g, 46 mmol) and 40μ copper powder (1.34 g, 21 mmol) and the resulting mixture refluxed under argon for 48 hours. The solution was filtered while hot, the insoluble material washed with warm pyridine and the filtrate evaporated to dryness. The residue was dissolved in benzene, treated with charcoal and evaporated to a crystalline residue. Crystallization from ethyl acetate gave 14.33 g (85%) of 3 as tan needles, mp 177°-178°. Recrystallization from ethyl acetate gave analytically pure 3, mp. 177°-178°. NMR (CDCl3): δ7.43-6.67, m(7), aromatic; 5.57, m(2), H5α and H8; 3.60, 3--OCH3 ; 3.03; 6--OCH3 ; 2.42, N--CH3 ; 1.17, d(3), 7--CH3, J=7 Hz.

Provenance & Evidence