Reference of 210532-25-5, These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, its 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.
A mixture of 1 (800 mg, 2.14 mmol) and dibutyltin dichloride (65 mg,0.21 mmol) in THF (13 mL) was stirred for 10 min at rt before 3,5-difluorobenzenesulfonyl chloride (500 mg, 2.35 mmol) dissolved in THF (2 mL)and 1,1,2,2,6-pentamethylpiperidine (0.77 mL, 4.27 mmol) were added underN2 atmosphere, and the resulting solution was stirred at rt o.n. The reactionwas quenched with sat. aq. NH4Cl followed by evaporation of the solvent; theresidue was diluted with CH2Cl2 and washed with water and brine. The organicphase was dried and evaporated. The obtained residue was dissolved inacetic anhydride (10 mL) and pyridine (10 mL) and stirred at rt o.n. An amorphouswhite solid was obtained after evaporation of the solvents to give crude2b, which was used directly in the following inversion. 1H NMR (CDCl3): delta7.47 (d, J = 8.1, 2H, Ph), 7.39-7.29 (m, 8H, Ph), 7.06 (d, J = 8.1, 2H, Ph), 5.38 (s, 1H, CH), 5.22 (t, J = 9.8, 1H, H-2), 4.82 (dd, J = 9.7, 3.6, 1H, H-3),4.61 (d, J = 9.8, 1H, H-1), 4.38 (m, 2H, H-4 and H-6), 4.01 (d, J = 12.5, 1H,H-6), 3.57 (s, 1H, H-5), 2.32 (s, 3H, CH3), 2.01 (s, 3H, Ac). 13C NMR (CDCl3): delta169.0, 137.1, 134.7, 129.7, 129.4, 128.4, 128.3, 126.6, 126.2, 111.1, 101.3, 85.0,80.5, 74.2, 69.5, 69.0, 66.5, 21.4, 20.9. HRMS calcd for [C28H26F2O8S2Na]+,615.0935; found: 615.0939.
Statistics shows that 3,5-Difluorobenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 210532-25-5.
Reference:
Article; Peterson, Kristoffer; Weymouth-Wilson, Alex; Nilsson, Ulf J.; Journal of Carbohydrate Chemistry; vol. 34; 8; (2015); p. 490 – 499;,
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