Dichloromethane → 1-Bromo-3-chloro-4-(methylthio)benzene

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Reaction Steps

Combine 1-methylsulfanyl-2-chloromethyl-benzene (3.7 g, 23 mmol), iron (−130 mg, 2.3 mmol), bromine (1.2 mL, 238 mmol), and dichloromethane (150 mL). Stir for 2 hours. Add water (10 mL), aqueous saturated sodium thiosulfate (100 mL) and ethyl acetate (100 mL). Separate the organic layer and wash with brine, dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with hexane to give 4.8 g of 4-bromo-2-chloro-1-methylsulfanyl-benzene (87%).

Provenance & Evidence