Bromine → 4-(1'-Methylcyclohexyl)bromobenzene

Participants

Reaction Steps

To 20.0 g (115 mmol) of the 1-methylcyclohexylbenzene obtained in the above-mentioned (1) were added 279 mg (5.00 mmol) of iron and 198 mg (0.78 mmol) of iodine, and 17.8 g (111 mmol) of bromine was slowly added dropwise at 0° C. spending 1.5 hours, followed by stirring at the same temperature for 1.5 hours and then at room temperature for 20 hours. The reaction solution was cooled and then quenched with 30 ml of saturated sodium sulfite aqueous solution and extracted three times with 50 ml of hexane. The combined organic layers were washed with 30 ml of sodium sulfite aqueous solution and 30 ml of water and dried with anhydrous sodium sulfate. After filtration of the desiccant, the solvent was recovered under a reduced pressure to obtain 27.9 g of crude bromide. By purifying the thus obtained crude bromide by distillation under a reduced pressure (from 117 to 120° C./2 mmHg), the specified substance was obtained with a yield of 80.3%.

Provenance & Evidence