Benzenesulfonyl chloride → HCID 59812105, compound

Participants

Reaction Steps

A mixture of iodide 36 (3.50 g, 13.0 mmol), PhSO2Cl (2.49 mL, 19.5 mmol), n-Bu4NHSO4 (0.57 g, 1.69 mmol) in CH2Cl2 (77 mL) was treated with 50% aq. NaOH (2.46 mL) then stirred for 40 min. It was then poured onto water (250 mL), the aqueous phase extracted with more CH2Cl2 (3×60 mL) and the combined organic extracts dried (MgSO4) and concentrated. Methanol was added to the resulting solid and the mixture stirred for 0.5 h. The solid was filtered off and washed with more methanol (2×) to afford iodide 37 as a white solid (4.00 g, 75%); 1H NMR (400 MHz, CDCl3) δ 7.46 (t, J=5.7 Hz, 2H), 7.59 (tt, J=7.5, 2.0 Hz, 1H), 7.93 (d, J=1.9 Hz, 1H), 7.95 (s, 1H), 8.16 (m, 2H), 8.60 (d, J=2.0 Hz, 1H).

Provenance & Evidence