[CH2:1]([C:9]1[CH:15]=[CH:14][C:12](N)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.N([O-])=O.[Na+].[I-:21].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.CCOCC>[I:21][C:12]1[CH:14]=[CH:15][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1To a suspension of 4-octylaniline (80.0 g, 389.6 mmol) in water (780 mL) was added aqueous HCl (40 mL) at room temperature. After the mixture was cooled to 0° C., more aqueous HCl (43 mL) was added, followed by dropwise addition of a solution of NaNO2 (26.9 g, 389.6 mmol) in water (195 mL). To the resulting arenediazonium salt solution was added dropwise a solution of potassium iodide (64.67 g, 389.6 mmol) in water (195 mL). The resulting mixture was heated with stirring at 40° C. After two hours, sodium thiosulfate was added to decolorize and the product was extracted with ether. The ethereal extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a crude oil. The crude material was dissolved in ether and filtered through a plug of silica gel three times and dried in vacuo to give 1-iodo-4-octylbenzene as a colorless oil. The product was used in the next step without further purification.
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