[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1.O.NN.[OH-].[K+]>COCCOCCOC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([F:12])([F:13])[F:14])[CH:3]=1A mixture of 1-(3-bromo-phenyl)-4,4,4-trifluoro-butan-1-one (3.1 g, 11 mmol) and diglyme was treated with hydrazine mono hydrate (5.5 g, 110.3 mmol), and stirred at 100° C. for 2 hours then treated with powder KOH (3.1 g, 55.1 mmol). The stirring continued at 150° C. for 6 hours. The mixture was cooled to room temperature, poured into a mixture of ice/water and extracted with ethyl ether. The extracts were combined, dried over MgSO4 and concentrated in vacuo. The crude product was purified on silica gel (ISCO) using hexanes as the eluting solvent to give 1-Bromo-3-(4,4,4-trifluoro-butyl)-benzene as a colorless oil (2.4 g, 88% yield). m/e (M)+ 266; 1H NMR (400 MHz, DMSO-d6) δ ppm, 1.7-1.8 (m, 2H), 2.1-2.2 (m, 2H), 2.6 (t, J=7.6 Hz, 2H), 7.2-7.25 (m, 2H), 7.3-7.35 (m, 1H), 7.4 (s, 1H)
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