1,4-Dichlorobenzene → HCID 18544379, compound

Participants

Reaction Steps

A mixture of 2-bromo-7-iodo-9,9-diprop-2-enylfluorene (major component) and 2,7-diiodo-9,9-diprop-2-enylfluorene (45.3 g, 0.1 mol), diphenylamine (17.0 g, 0.1 mol), potassium carbonate (30.38 g, 0.22 mol), copper bronze (4.8 g, 76 mmol), copper(I) iodide (1.0 g, 5.25 mmol), dichlorobenzene (85 mL) and toluene (50 mL), was heated to reflux, and toluene and water were distilled off to get a reaction temperature of 182-183° C. After 7 hours, the reaction was cooled, diluted with 100 mL methylene chloride and filtered. The salts were washed with 3×50 mL methylene chloride. The combined filtrate was concentrated and chromatographed over a column of alumina (800 g). Elution with 10% toluen-heptane gave the product, 27.21 g, 55% yield, m.p. 141.4-143.3° C. Mass Spec: m/z 539 (M+, iodo analog), 491,493 (M+, desired bromo). Anal. Calcd. for C31H26BrN: C, 75.61%; H, 5.32%; N, 2.84%; Br, 16.23%. Found: C, 74.02%; H, 5.37%; N, 2.68%; Br, 12.42%; I, 6.19%.

Provenance & Evidence