Dichloromethane → HCID 58934931, compound

Participants

Reaction Steps

To a suspension of 1.5 g (5.2 mmol) of 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid in 45 mL of anhydrous dichloromethane was added dropwise a solution of 1.0 M sulfuryl chloride (22.75 mmol, 4.4 eqv). The resulting suspension was stirred at room temperature for 12 h; the reaction turned into a clear yellow solution. The sample was concd and the residue dissolved in ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. Silica chromatography with ethyl acetate:hexane:acetic acid as the eluant afforded 0.12 g (21.5%) of a white solid: 1H NMR (CDCl3/400 MHz) 7.72(s, 1H), 6.68(s, 1H), 5.79(q, J=5.6 Hz, 1H), 2.42(m, 1H), 2.11(m, 1H), 0.85(t, J=7.6 Hz, 3H). MS (ESI+) 357.0 (M+1, 100). MS(ES−) 355.0 (M−H, 100). HRMS (ES−) m/z calcd for (C13H8Cl2F3O4) M−H: 354.9746, found: 354.9724.

Provenance & Evidence