Acetic Acid → 2-[(Benzenesulfonyl)methyl]-4-bromo-1-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-bromo-4-nitrobenzene (5.05 g, 25 mmol) and chloromethyl-phenylsulfone (4.76 g, 25 mmol) in dry THF (50 mL) at −65° C. under nitrogen is added 1.0M KOtBu in THF (55 mL, 55 mmol). The deep purple reaction is allowed to warm to 0° C. over 1.5 hours and then treated with glacial acetic acid (4 mL). The reaction is diluted with water (100 mL) and saturated aqueous NaHCO3 (100 mL), and then extracted with CH2Cl2 (2×200 mL). The extracts are dried (MgSO4) and concentrated in vacuo to a light orange solid. Trituration with ethyl acetate and hexanes affords the title compound as a pale yellow solid (6.45 g, 72%). Mp: 143-144° C. MS (ES−): 354 (M−H).

Provenance & Evidence