[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Cl:11])[C:7]=1[CH:8]([F:10])[F:9].Br[C:22]([C:24]([F:27])([F:26])[F:25])=[CH2:23].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:6]1[CH:5]=[C:4]([C:22]([C:24]([F:27])([F:26])[F:25])=[CH2:23])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH:8]([F:9])[F:10]
A mixture of 2-(3,5-dichloro-4-(difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (0.58 g, 1.8 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (0.45 g, 2.5 mmol), Cs2CO3 (1.8 mL, 2M, 3.6 mmol) and Pd(PPh3)2Cl2 (38 mg) in THF (10 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel eluted with hexanes to give 1,3-dichloro-2-(difluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (0.33 g; yield 62%) as colorless oil. 1H NMR (500 MHz, CDCl3): δ 7.381 (s, 2H), 7.045 (t, J=53.0 Hz, 1 H), 6.049 (s, 1 H), 5.820 (s, 1 H) ppm.
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