[I:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:13][C:14]([O-])(C)[CH3:15].[K+].C1COCC1.C(Br)C=C>O>[CH2:15]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:2]=1[I:1])[CH:14]=[CH2:13]
To a mixture of 2-iodo-4-trifluoromethyl-aniline (5 g, 17.4 mmol), KOt-Bu (2.05 g, 18.3 mmol) and THF (200 mL) at −78° C., is added allyl bromide (2.21 g, 18.3 mmol). The resulting mixture is warmed to rt and stirred for 18 h. Water is added, and the mixture is extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-50% EtOAc in heptane to afford allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine (1.9 g, 33%). MS 328 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.90 (s, 1H), 7.45 (d, 1 H), 5.88-6.02 (m, 1H), 5.33 (d, 1 H), 5.25 (d, 1H), 4.72(broad s, 1H), 3.90 (s, 2H).
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