70 mL), and HOAc 300 (13.20 mL) was heated to 100 °C for 4 h. The resulting mixture was 301 then cooled to 0 °C and basified to pH 9 with an aqueous NaOH 302 solution (2 M) Ethyl acetate (100 mL) was added, and the mixture 303 was washed successively with an aqueous NaHSO 3 solution and brine. 304 The combined organic layers were dried over MgSO 4 , and the solvent 305 was evaporated. The residue was purified over silica (10% EtOAc in 306 petroleum ether as the solvent) The desired fractions were combined 307 and the solvent evaporated, yielding the title compound as oil (0.655 g, 308 1.83 mmol) Yield: 76%. R f : 0.33 (10% EtOAc in petroleum ether on 309 silica). 1 H NMR (400 MHz, CDCl 3 ): ? 8(trifluoromethyl)phenyl)methyl)pyridine L3, L2. A mixture of the 299 A2 (0.900 g, 2.41 mmol), aqueous 57% HI62?8.56 (m, 1H), 7.62?7.56 310 (m, 1H), 7.31 (s, 4H), 7.10 (s, 6H), 5.62 (s, 1H)-MS (ASAP + ) [M + H] + 313 Calculated equiv) and PBr 3 (25 mL) was vigorously 316 stirred and heated and kept at 110 °C for 2 h. The mixture was then 317 cooled to r.t. and was carefully poured onto ice, and aqueous NaOH ,
75 (s, 1H) 13 C NMR 332 (126 MHz, CDCl 3 ): ? 161, pp.382-382, 1030. ,
Andrews and 409 EPSRC (EP/M02105X/1) for financial support We thank 410 Umicore AG for the gift of materials. We thank the EPSRC UK 411 National Mass Spectrometry Facility at Swansea University for 412 analytical services. T.R. thanks the FEDER funds for financial 413 support helping the acquisition of the D8Venture diffractom- 414 eter of ISCR. D.J. acknowledges the European Research 415 Council and the Re?gionRe?gion des Pays de la Loire for financial 416 support in the framework of a Starting Grant (Marches 417 -278845) and the LUMOMAT RFI project, respectively. This 418 research used computational resources of (1) the GENCI- 419 CINES, IDRIS, issue.231, p.422 ,
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An efficient synthesis 626 ,