Imidazole → 6-Bromo-1-(1-imidazolyl)-3,4-dihydronaphthalene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.S(Cl)(Cl)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)=[CH:7][CH2:6][CH2:5]2Participants
4
Procedure
Analogously to Example 1, 2.25 g of 6-bromo-1-tetralone are reacted with 1.36 g of imidazole and 0.873 ml of thionyl chloride, yielding the title compound, which is purified by column chromatography (SiO2, hexane/ethyl acetate 9:1 to 1:1) and crystallisation from hexane/ether; m.p. 58°-64°, 1H-NMR (CDCl3): δ (ppm)=0.43 (m, 2H), 2.9 (m, 2H), 6.12 (t, 2H), 6.63 (d, 1H), 7.02 (d, 1H), 7.18 (d, 1H), 7.28 (dd, 1H), 7.36 (d, 1H), 7.61 (s, 1H).
Sources & evidence
- ORD record
- ord-232c419ac24b40dd8000f344fd12ed73