Electric Literature of 220227-21-4,Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Synthesis of N-{5-[l-(2,4-Dichloro-benzyl)-5-fluoro-3-methyl-lH-indol-7-yl]- [l,3,4]oxadiazol-2-yl}-2,4,5-trifluoro-benzenesulfonamide, B12. A solution of 2,4,5-trifluorobenzenesulfonyl chloride (92 mg, 0.4 mmol, 4 equiv.) in pyridine (0.3 mL) was added to a mixture of 1-14 (39 mg, 0.1 mmol, 1 equiv.) and DMAP (49 mg, 0.4 mmol, 4 equiv.) at rt. The reaction mixture was heated to 90 0C for 2 h. The reaction mixture was then quenched with 10% aqueous HCl and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting oil was chromatographed on SiO2 (0.5 g), eluting with CH2Cl2 to afford B12 (10 mg, 17 %) as a yellow oil. Rf= 0.40 (EtOAc). 1H-NMR (400 MHz, CDCl3) 2.34 (d, J =1.2 Hz, 3H), 5.64 (s, 2H), 6.05 (d, J = 8.4 Hz, IH), 6.97 (dd, J = 8.4, 2.0 Hz, IH),7.03 (s, IH), 7.08 (m, IH), 7.29 (dd, J = 9.6, 2.4 Hz, IH), 7.35 (d, J = 2.0 Hz, IH), 7.51 (dd, J = 8.4, 2.4 Hz, IH), 7.86 (m, IH). LC-MS (95 %): ESI” Calcd. 586 (M) Found: 585.1 (M-I).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,5-Trifluorobenzene-1-sulfonyl chloride, its application will become more common.
Reference:
Patent; DECODE CHEMISTRY, INC.; WO2006/44405; (2006); A1;,
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