Reaction SMILES: C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH:31]=[O:32].Cl.CC1(C)CCCC(C)(C)[NH+]1[O-].C(=O)(O)[O-].[Na+].Cl[O-].[Na+]>O.C1COCC1>[C:13]1([S:19]([C:22]2[C:27]([C:31]([C:30]3[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=3[Cl:28])=[O:32])=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:20])=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
Reactant: O=Cc1ccccc1Cl
Reactant: O=S(=O)(c1ccccc1)c1ccccn1
Agent: CC1(C)CCCC(C)(C)[NH+]1[O-]
Agent: Cl
Agent: O=C([O-])O
Solvent: C1CCOC1
Solvent: CC(C)NC(C)C
Solvent: O
Product: O=C(c1ccccc1Cl)c1cccnc1S(=O)(=O)c1ccccc1
Temperature: -65 °C
Reaction time: 0.5 h
Yield: 80 %

Procedure:
A solution of 1.3 eq of diisopropylamine (based on 2-benzenesulfonyl pyridine) in 5 volumes of THF in a mechanically stirred 3-necked flask is cooled to −70 to −75° C. To this solution is added 1.05 eq of n-butyllithium (1.6M in hexanes) at such a rate as to maintain the temperature below −60° C. The light yellow solution is stirred at −60 to −70° C. for 30 minutes. Once the temperature has cooled back down to −60 to −65° C., 1.0 eq of 2-benzene-sulfonyl pyridine, as a solution in 3 volumes of THF, is added at the fastest rate that will maintain the reaction temperature under −60° C. A yellow suspension forms during the addition that becomes yellow-orange upon longer stirring. This mixture is stirred for 3 hours at −60 to −75° C., and then 1.06 eq of 2-chlorobenzaldehyde, as a solution in 1 volume of THF, is added dropwise at a sufficient rate to keep the temperature under −55° C. The suspension gradually turns orange-red, thins out, and then becomes a clear red solution. The reaction mixture is allowed to stir at −60 to −70° C. for 1 hour, 3N aqueous HCl (7 volumes) is added over 20-30 minutes, and the temperature is allowed to exotherm to 0-10° C. The color largely disappears, leaving a biphasic yellow solution. The solution is warmed to at least 10° C., the layers are separated, and the aqueous layer is back-extracted with 10 volumes of ethyl acetate. The combined organic layers are washed with 10 volumes of saturated sodium bicarbonate solution and concentrated to about 2 volumes. Ethyl acetate (10 volumes) is added, and the solution is once again concentrated to 2 volumes. The thick solution is allowed to stand overnight and is taken to the next step with no purification of the crude alcohol intermediate. The crude alcohol intermediate is transferred to a 3-necked flask with enough ethyl acetate to make the total solution about 10 volumes. The yellow solution is treated with 3.2 volumes of 10% aqueous (w/w) potassium bromide, followed by 0.07 eq of 2,2,6,6-Tetramethylpiperidine-N-oxide (TEMPO). The orange mixture is cooled to 0-5° C. and treated with a solution of 1.25 eq of sodium bicarbonate in 12% w/w sodium hypochlorite (9 volumes) and 5 volumes of water over 30-60 minutes while allowing the temperature to exotherm to a maximum of 20° C. The mixture turns dark brown during the addition, but becomes yellow, and a thick precipitate forms. The biphasic light yellow mixture is allowed to stir at ambient temperature for 1-3 hours, at which time the reaction is generally completed. The biphasic mixture is cooled to 0-5° C. and stirred for 3 hours at that temperature. The solid is filtered off, washed with 4 volumes of cold ethyl acetate, followed by 4 volumes of water, and dried in vacuo at 45° C. to constant weight. Typical yield is 80-83% with a purity of greater than 98%. 1H NMR (600 MHz, CDCl3-d) δ ppm 7.38 (td, J=7.52, 1.28 Hz, 1H) 7.47 (dd, J=7.80, 1.30 Hz, 1H) 7.51 (td, J=7.79, 1.60 Hz, 1H) 7.51 (t, J=7.89 Hz, 2H) 7.50-7.54 (m, J=7.75, 4.63 Hz, 1H) 7.60 (t, J=7.43 Hz, 1H) 7.73 (dd, J=7.75, 1.60 Hz, 1H) 7.81 (dd, J=7.79, 1.56 Hz, 1H) 8.00 (dd, J=8.44, 1.10 Hz, 2H) 8.76 (dd, J=4.63, 1.61 Hz, 1H).