2-(Trifluoromethoxy)benzene-1-sulfonyl chloride

White crystal

a) 5-Methyl-3-(2-trifluoromethoxyphenylsulfonyloxy)phenol Orcinol monohydrate (1.42 g, 10.0 mmol) and 2-trifluoromethoxybenzenesulfonyl chloride (2.35 g, 9.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3 x 50 mL). The organic phase was washed with brine (2 x 50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a yellow oil (1.80 g, 57%). 1H-NMR (300 MHz, CDCl3) delta 7.96 (d, J = 7.9 Hz, 1H), 7.72 (t, J = 7.8 Hz, 1H), 7.50 (d, J = 8.1 Hz, 1H), 7.40 (t, J = 7.8 Hz, 1H), 6.55 (s, 1H), 6.52 (s, 1H), 6.41 (s, 1H), 5.04 (s, 1H); 2.23 (s, 3H).General procedure: To a solution of 1, 3-dihydro-2H-imidazol-2-one (10, 12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil, 17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac).

Molecular Weight:260.62
XLogP3:3.1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:259.9521773
Monoisotopic Mass:259.9521773
Topological Polar Surface Area:51.8
Heavy Atom Count:15
Complexity:308
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes