[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[Na+].Cl[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16].O>CS(C)=O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:13]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=2[C:15]#[N:16])=[CH:5][CH:4]=1
To a solution of 11.55 g (0.0824 moles) of 4-(methylthio)phenol dissolved in 150 ml of DMSO was added 3.3 g (0.0824 moles) of NaOH. The slurry was heated to 60° C. and 13.7 g (0.0730 moles) of 2-chloro-5-nitrobenzonitrile was added and the mixture heated at 75° C. for 21/2 hrs. The mixture was cooled and poured into a solution of 200 ml of 5 N aqueous NaOH and 500 ml of water. The product was collected by filtration, washed well with water and dried, to obtain 20.3 g of product (94.6% yield). Recrystallization from methanol afforded purified 2-(4-(methylthio)phenoxy)-5-nitrobenzonitrile, mp 124°-126° C.
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