Benzenesulfonyl chloride → HCID 59811927, compound

Participants

Reaction Steps

To a solution of 2 (6.00 g, 16.5 mmol) in benzene (100 mL) was added benzenesulfonyl chloride (4.85 mL, 38.0 mmol), tetra-n-butylammonium bromide (2.82 g, 8.76 mmol) and 50% aqueous NaOH (18.5 mL), and the reaction mixture was stirred overnight. The mixture was partitioned between water—benzene. The layers were separated and the aqueous layer was extracted with benzene (5×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give orange oil, which solidified on drying in vacuum. The solid was triturated with methanol (200 mL) for 0.5 h, filtered off, and washed with ice-cold methanol (3×50 mL) to give product 3 as a tan solid (5.32 g, 64%); 1H NMR (400 MHz, CDCl3) δ 3.01 (s, 6H), 6.81 (d, J=8.9 Hz, 2H), 7.45-7.60 (m, 4H), 7.59 (tt, J=14.8, 2.1 Hz, 1H), 7.74 (d, J=2.1 Hz, 1H), 7.86 (s, 1H), 8.24 (d, J=7.6 Hz, 2H), 8.64 (d, J=2.1 Hz, 1H); MS (CI) m/z 504.10 (MH+).

Provenance & Evidence