Alkylation and halogenation of sulfones proceed smoothly using NaOH in DMF.E.g., alkylation of RCH2SO2R1 (I; R = 2,5-Me2C6H3, R1 = 1-oxopyrid-2-yl) with R2Cl (R2 = Me, CH2:CHCH2) in NaOH/DMF gave 74-92% RCHR2SO2R1 (R-R2 as before), whereas halogenation of I (R = naphth-2-yl, R1 as before) with CCl4 in NaOH/DMF gave 96% RCHClSO2R1 (R, R1 as before).In addition, both halogenation and alkylation can be performed in the same flask to obtain α-disubstituted products.Thus, PhCH2SO2R (R = 1-oxopyrid-2-yl) underwent sequential treatment with CCl4 and MeI in NaOH/DMF to give 77% PhCClMeSO2R (R as before).