Hydrochloric Acid → 3-n-Hexyl-5-methylbromobenzene

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After adding anhydrous tetrahydrofuran (2 L), 3,5-dibromotoluene (477 g, 1.91 mol) and 1,1-bis(diphenylphosphino)ferrocene dichloropalladium(II) dichloromethane complex (Pd(dppf).CH2Cl2, CAS:851232-71-8, 6.24 g, 7.64 mol) in a 6 L flask under an inert gas atmosphere, the mixture was stirred at 57° C. for 15 minutes. Next, solution 1-1 was added dropwise at rate which maintained a temperature of no higher than 60° C., and the mixture was stirred at 57° C. for 2 hours. The reaction mixture was then added to 10 wt % hydrochloric acid that had been cooled with an ice bath, and stirred, and extraction was performed with toluene. The obtained organic layer was rinsed twice with water and the organic layer was concentrated under reduced pressure to remove the solvent. This was followed by vacuum distillation and purification by column chromatography, to obtain 326 g of the target 3-n-hexyl-5-methylbromobenzene (compound 1-1 represented by the following formula).

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