1,1′-Sulfinylbis[4-chlorobenzene]

SLIGHTLY YELLOW TO LIGHT BEIGE FINE CRYST. POWDER

General procedure: The reactions were conducted in the fume hood at 25 Cand 70 C, respectively, with the molar ratio of PhX:SOCl2:AlCl3 being 2:1:1 and usage of SOCl2 approximately 10 mmol. For eachreaction, granular AlCl3 was added piecewise to the PhX-SOCl2 mixture (X=CH3 or Cl) in a large test tube (~ 80 mL) as follows: First, one piece of AlCl3 was added and gas (HCl) bubbles started to form immediately. The piece of AlCl3 was crushed using a stirring rod. When most of the piece of AlCl3 had dissolved and bubbling occurredvery slowly, another piece of AlCl3 was added. All the AlCl3 granules were eventually added into the PhX-SOCl2 mixture piece-by-piece. The solution was initially light green and it turned dark green as the reaction went to completion, indicated by ceasing of bubbling after all the AlCl3 had been added. Then iced water (40 mL) was poured into thereaction mixture and the green colour disappeared. This was followed by addition of diethyl ether (20 mL). All the contents were transferredinto a separating funnel and shaken well to assure the organic productbeing fully extracted into the ether phase. The ether and water phaseswere separated. The water phase was extracted by diethyl ether (20 mL) again. Then all the ether solutions were combined and dried by anhydrous sodium sulfate. The dried ether solution was filtered off and left in the fume hood. Eventually, all the diethyl ether solvent evaporated, giving the final reaction product. The product was thencharacterised by GC-MS, and the results are shown in Table 1.General procedure: Approach 1: The reactions were conducted in the fumehood at0C with the molar ratio of PhCl : SOCl2 : MCl3 being 1:1:1and usage of SOCl2 approximately 10 mmol [PhCl (1.13 g, 10.0 mmol), SOCl2 (1.19 g, 10.0 mmol), and AlCl3 (1.33 g, 10.0 mmol) or FeCl3 (1.62 g, 10.0 mmol)]. For each reaction, SOCl2 was added dropwise to the PhCl-MCl3 (M = Fe or Al)mixture in a large test tube (80 mL) with constant stirring (Forthe AlCl3-catalyzed reaction, SOCl2 was added after the granular AlCl3 had been mostly crushed). The reaction took placequickly, indicated by bubbling (formation of HCl) as above.After all the SOCl2 was added, the reaction went to completion(in about 2 h), indicated by the cessation of bubbling. Then icedwater (40 mL) was poured into the reaction mixture. This wasfollowed by the addition of diethyl ether (20 mL). All the contents were transferred into a separatory funnel and shaken well to ensure that the organic product had been fully extracted intothe ether phase. The ether and water phases were separated. Thewater phase was extracted by diethyl ether (20 mL) again. Thenall the ether solutions were combined and dried by anhydroussodium sulfate. The dried ether solution was fltered o and leftin the fumehood. Eventually, all the diethyl ether solvent evaporated, giving the fnal reaction product. The product was thencharacterized by GC-MS, and the results are shown in Table 1(Entry 1).(1) chlorobenzene and thionyl chloride are subjected to a Friedel-Craft reaction under the action of a catalyst to obtain (1) performing a Friedel-Craft reaction of thionyl chloride and chlorobenzene under the action of a catalyst, The reaction temperature of the Friedel-Crafts is 30 C for 1 h, and the molar ratio of thionyl chloride to chlorobenzene is 1:4.The catalyst is anhydrous aluminum trichloride and benzyl triethyl ammonium chloride in a mass ratio of 3:1;(2) After the end of the mixed reaction, the temperature was lowered to 10 C for 1 h, and then heated to 100 C for 2 h.Then cooling, crystal precipitation, filtration to obtain

Molecular Weight:271.2
XLogP3:4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:269.9672914
Monoisotopic Mass:269.9672914
Topological Polar Surface Area:36.3
Heavy Atom Count:16
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes