[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[F:14])(=[O:3])[CH3:2].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH:6]([Br:15])[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[F:14])(=[O:3])[CH3:2]A solution of 4-bromo-2-fluorophenethyl acetate (2.72 mmol) in carbon tetrachloride (6 mL) was degassed with a stream of nitrogen for five minutes, at which point the solution was treated with N-bromosuccinimide (2.99 mmol) and azobisisobutyronitrile (0.272 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture stirred at 80° C. for 8 h, at which point the reaction was cooled to room temperature and was stirred overnight. The resulting mixture was concentrated to dryness in vacuo. Purification of the crude material by silica gel chromatography (0-50% ethyl acetate/hexanes) afforded the title compound as a beige oil (790 mg, 77% yield). 1H NMR (400 MHz, DMSO-d6) d ppm 2.00 (s, 3 H) 4.57 (dd, J=11.62, 7.07 Hz, 1 H) 4.67 (dd, J=11.75, 7.20 Hz, 1 H) 5.52 (t, J=7.07 Hz, 1 H) 7.45-7.55 (m, 1 H) 7.59-7.70 (m, 2 H).
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