Sodium Hydroxide → 4-Bromo-1-chloro-2-ethylbenzene
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[OH-].[Na+].O.NN.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([C:13](=O)[CH3:14])[CH:12]=1>C(O)COCCOCCO>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([CH2:13][CH3:14])[CH:12]=1[OH-].[Na+].O.NN.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([C:13](=O)[CH3:14])[CH:12]=1>C(O)COCCOCCO>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([CH2:13][CH3:14])[CH:12]=1Sodium hydroxide (0.39 g, 9.6 mmol) and hydrazine monohydrate (0.56 mL, 11.5 mmol) were added to a solution of 1-(5-Bromo-2-chloro-phenyl)-ethanone (0.9 g, 3.85 mmol) dissolved in triethylene glycol (5 mL). The reaction mixture was heated to 170° C. for 24 hours and then partitioned between 1N HCl and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound (0.52 g, 62%). 1H NMR (400 MHz, CDCl3): δ 1.23 (t, J=7.6 Hz, 3 H), 2.72 (q, J=7.6 Hz, 2 H), 7.19 (d, J=8.6 Hz, 1 H), 7.25 (dd, J=8.3, 2.3 Hz, 1 H), 7.36 (d, J=2.5 Hz, 1 H).
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