Hydrogen Bromide → 1,3-Bis(3,5-dibromophenyl)adamantane

Participants

Reaction Conditions

Reaction Steps

After the air inside a 1 litter flask equipped with a thermometer and stirrer was replaced by nitrogen, 43 g of 1,3-dibromoadamantane and 10 g of anhydrous aluminum bromide were placed therein, and then the inside of the flask was cooled to 0° C. Thereto was added 190 g of 1,3-dibromobenzene that was cooled to 5° C. in advance, and the resulting material was agitated and reacted at an inside temperature of 0 to 10° C. for 7 hours. The reaction was carried out while the hydrogen bromide gas that was generated during the reaction was absorbed into an aqueous alkaline solution for the removal of its toxicity. After the completion of the reaction, 130 g of 4% by weight hydrochloric acid was slowly dropped and then the solution was stirred until the orange color of the reaction solution faded away. The agitation was stopped and the resulting solution was allowed to stand and then separated by funnel. The resulting organic phase was washed with water three times. 190 grams of toluene was added to the organic phase after the washing, which was then warmed to remove water under reflux. Then, the organic solution was cooled and the crystal deposited was collected by filtration. The resulting crystal was subjected to washing with toluene, methanol and water, followed by drying under reduced pressure to obtain 44 g of 1,3-bis(3,5-dibromophenyl)adamantane.

Provenance & Evidence