Benzenesulfonyl chloride, 2,4-dichloro- → HCID 59864836, compound

Participants

Reaction Steps

To a room temperature solution of 3.3 (29 mg, 0.079 mmol) dissolved in pyridine (2 mL) was added 2,4-dichlorobenzenesulfonyl chloride (21 mg, 0.087 mmol). The resulting red solution was stirred at room temperature for 2 h, after which time HPLC indicated no 3.3 remained. The reaction solution was concentrated in vacuo on a rotary evaporator and the concentrate partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic separation was washed with water then brine. The organic extract was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford an orange oil. The product was isolated by chromatography on silica gel, eluting with an ethyl acetate/hexane gradient, to afford a faint yellow oil. 1H NMR (500 MHz) (CDCl3) δ 7.71 (d, J=8.4 Hz, 1H); 7.48 (s, 1H); 7.04 (d, J=8.8 Hz, 1H); 6.88 (d, J=1.8 Hz, 1H); 6.70 (s, 1H); 6.59 (d, J=8.7 Hz, 1H); 6.53 (d, J=6.4 Hz, 1H); 6.52 (d, J=1.8 Hz, 1H); 6.16 (d, J=8.2 Hz, 1H); 4.19 (q, J=7.1 Hz, 2H); 3.86 (s, 3H); 3.64 (s, 3H); 3.59 (s, 2H); 2.48 (s, 3H) ppm.

Provenance & Evidence