S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]O)=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1.N1C=CC=CC=1.C(Cl)[Cl:25]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][Cl:25])=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1
12 g thionyl chloride (7.4 ml, 100 mmol) in 10 ml toluene (abs.) are quickly added in a drop-wise manner to a solution of 6.78 g 2-(4-chloro-2-nitrophenyl)ethanol (33 mmol) in 100 ml abs. toluene and 2.5 ml pyridine. This is heated 2 h under reflux, cooled, poured onto 100 g ice and mixed with 100 ml CH2Cl2. The aqueous phase is extracted 2× each with 50 ml CH2Cl2. The combined organic phases are neutralized 2× each with 80 ml saturated bicarbonate solution, dried over Na2SO4, filtered and rotary evaporated. 7.12 g (32 mmol, 98%) 2-(4-chloro-2-nitrophenyl)ethyl chloride are obtained as a brown oil which hardens to a brown solid after some days in the refrigerator.
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