In a
500-ml., three-necked, round-bottomed flask fitted with a
stirrer, a
reflux condenser, and a
dropping funnel are placed
8.08 g. (0.040 mole) of pyrene (Note
1) and
80 ml. of carbon tetrachloride (Note
2). A solution of
2.0 ml. of bromine (6.24 g., 0.039 mole) (Note
3) in
30 ml. of carbon tetrachloride is added dropwise over a period of 2–3 hours. The resulting orange solution is stirred overnight, washed with three 100-ml. portions of water, and dried over anhydrous
calcium chloride. The solvent is removed under reduced pressure, the pale yellow solid residue is dissolved in
10 ml. of benzene, and the
benzene solution is treated with a small amount of activated
carbon. The filtrate is diluted with
120 ml. of absolute ethanol, and the solution is distilled until about 80–90 ml. of solvent remains and then cooled. The
bromopyrene crystallizes as pale yellow flakes, m.p.
93–95°. Additional material of similar melting point is obtained from the mother liquor on concentration. The total yield is
8.5–9.5 g. (
78–86%) (Note
4). On recrystallization from
benzene-alcohol a colorless product, m.p.
94.5–95.5°, is obtained with little loss.