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With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;
General procedure: To a solution of bromobiphenyl aldehyde 11 (390 mg, 1.5 mmol) and 4-fluoro phenyl boronic acid 12a (209.8 mg, 1.5 mmol) in 2 M aqueous sodium carbonate (2 mL) and toluene/ethanol (12:4 mL) is added a catalytic amount (0.4 mol %) of tetrakis-triphenylphosphine palladium, and the mixture was heated to reflux under argon atmosphere for 3-4 h. After completion of the reaction, the reaction mixture is cooled to room temperature and extracted with ethyl acetate (3 x 30 mL) and the organic phase was extracted with water and brine solution, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to get the crude product. This crude product was further purified by column chromatography (10% ethyl acetate and hexane) to afford the pure terphenyl aldehydes (13a) as a white solid in 310 mg, 74% yield; mp: 135-136 C; 1H NMR (300 MHz, CDCl3): δ 7.12-7.19 (m, 2H), 7.57-7.73 (m, 6H), 7.78 (d, 2H, J = 8.3 Hz), 7.96 (d, 2H, J = 8.3 Hz), 10.06 (s, 1H); (ESI) MS: m/z 277 (M+H)+.
4-(3,4,5-trifluorophenyl)-3-fluorotoluene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
9.5 g
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; at 100℃; under 18751.9 Torr; for 17h;Autoclave;
[0168] (13-2) A solution prepared by suspending 3-fluoro- 4-iodotoluene (12.0 g) produced in 13-1, 3,4,5-trifluorophe- nylboric acid (9.0 g), anhydrous potassium carbonate (4.1 g), and tetrakis-triphenylphosphine palladium(0) (0.33 g) in ethanol (60 mE) was heated to 1000 C. (2.5 MPa) in an autoclave and then stirred for 17 hours. Afier the solution was allowed to cool to room temperature, toluene and water were added to separate an organic layet The organic layer was washed with saturated brine and then dried with sodium sulfate. The sodium sulfate was filtered off, and the organic solvent was distilled off under reduced pressure. Then, the residue was purified by silica gel column chromatography to yield 9.5 g of 4-(3,4,5-trifluorophenyl)-3-fluorotoluene as a colorless solid.