[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][C:17]3=[O:20])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:21]Br.C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>Cl.C(Cl)Cl>[Br:21][CH:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][C:10]([NH:9][C:7](=[O:8])[CH2:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:11][CH:12]=2)[C:17]1=[O:20]
To a mixture of 7-cyclopentylacetamido-1-tetralone (1.02 g) in ethereal HCl (0.2 ml) and methylene chloride (20 ml) was added a solution of bromine (0.19 ml) in a mixture of ethereal HCl (10 drops) and carbon tetrachloride (1 ml). The reaction was stirred for 3 h and ethyl acetate (60 ml) was added. The mixture was washed (saturated sodium bicarbonate, water, brine), dried (MgSO4), and evaporated. The residue was recrystallized from methylene chloride and petroleum ether to give 2-bromo-7-cyclopentylacetamido-1-tetralone (1.23 g, 95%) as a colorless solid; mp 162.5°-164.0° C.
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