2,3,6,7,14,15-Hexabromo-9,10-dihydro-9,10-[1,2]benzenoanthracene

Uses

2,3,6,7,14,15-Hexabromo-9,10-dihydro-9,10-[1,2]benzenoanthracene can be used as impurity standard and reference substance, mainly used in laboratory research and development process and chemical production process middle.

Synthesis

Triptycene (1.06 g, 4.18 mmol) was dissolved in chloroform (80 mL) in a round-bottom flask. Iron filings (30 mg) were added, and the solution was stirred at 25 C. Bromine (1.35 mL, 26.3 mmol) was added, and the solution was refluxed for 1 h, during which time the initially reddish-brown solution turned reddish-orange. The flask was removed from heat, and chloroform and excess bromine were removed under vacuum. The resulting brown powder was dissolved in chloroform (100 mL) and flushed through a pad of silica using additional chloroform as eluent (100 mL). The filtrate was evaporated to dryness. The crude white powder (2.83 g, 98%) was crystallized from acetone yielding C20H8Br6 ¤ (acetone)2 (0.88 g, 29%), mp >350 C. The mother liquor was evaporated and the residue was crystallized from acetone to afford a second crop of crystals (0.97 g, C20H8Br6 ¤ (acetone)2, 32%). The combined yield was 1.85 g, 61%: 2-H yield 2.83 g, 98%