Water → HCID 22066277, compound

Participants

Reaction Conditions

Reaction Steps

2-bromo-5,3′-bis-octyloxy-biphenyl (0.598 g, 1.225 mmol) prepared in Example 3 was dissolved in dried THF (30 ml) and cooled to −78° C. Then, 5-butyllithium (t-BuLi) (1.7M, 1.44 ml, 2.45 mmol) was added slowly. The obtained resultant was stirred for about 1 hour at −78° C. After 1 hour, 2,7-dibromofluorene-9-on (0.497 g, 1.47 mmol) dissolved in dried THF (20 ml) was added slowly, stirred for about 1 hour, allowed to warm to room temperature and further stirred at room temperature for about 30 minutes. A small amount of distilled water was added to complete the reaction and saturated brine was added to the resultant. The organic layer was filtered twice with ether and dried over sulfate, and the ether was concentrated under reduced pressure. Purification by silica gel chromatography using 30 to 40% dichloromethane in hexane gave 9-(5,4′-bis-octyloxy-biphenyl-2-yl)-2,7-dibromo-9H-fluorene-9-ol corresponding to the compound IV of the reaction scheme 1 (Yield: 0.62 g, 68%), R1 and R2 in the formula of the compound IV being each independently octyl and X being boron. The product was identified through the NMR spectrum and element analysis that it had the identical structure with the compound IV.

Provenance & Evidence