Hydrochloric Acid → HCID 59297263, compound

Participants

Reaction Steps

To a stirred mixture of 2,7-dibromo-3-methoxyfluorene (87.7 g, 0.244 mol), potassium t-butoxide (28 g, 0.25 mol) and dry methyl sulfoxide (500 mL) was added 1-bromopropane (22.6 mL, 0.25 mol) at such a rate as to keep the reaction exotherm temperature below 45° C. A further quantity of potassium t-butoxide (39.0 g; 0.35 mol) and 1-bromopropane (31.6 mL; 0.35 mol) were added. The resulting mixture was stirred at room temperature for 1 hour and treated with 50% methanol/water (500 mL). The purple color was discharged by addition of 6.0M hydrochloric acid (2.0 mL) and the mixture cooled at 0° C. for 1 hour. The crude product was collected and washed with 50% methanol/water (250 mL) and dried to yield crude product (106 g). Purification by extraction from neutral alumina (5 cm3) with hexane on an Ace-Kauffman column with hexane afforded 2,7-dibromo-9,9-dipropyl-3-methoxyfluorene (95 g; m. pt. 127-131.5° C.). Further purification by re-crystallization (2-propanol) gave pure product (84 g, yield 78%).

Provenance & Evidence