Hydrochloric Acid → HCID 10811027, compound

Participants

Reaction Steps

Butyllithium (48.2 mmol, 30.2 ml, 15% in hexane) was added into a solution of 1,4-dibromo-2,5-dihexyloxybenzene (48.2 mmol, 21.0 g) in ether (195 ml) under argon at between -10° to -30° C. over 15 min. The mixture was allowed to warm to room temperature and was stirred for further 2 h. It was then transferred into a solution of freshly distilled trimethyl borate (145 mmol, 16.4 ml) in ether (390 ml) under argon at -60° C. The mixture was allowed to warm to room temperature and was stirred for further 15 h. Aqueous hydrochloric acid (2M, 300ml) was added into the mixture, and the aqueous layer was separated and extracted with ether (100 ml×2). The combined organic layer was evaporated and 40/60 petroleum ether (200 ml) was added. A colourless solid was recovered by filtration and dried under vacuum. Further purification was carried out by column chromatography over silica (60 g), with toluene (200 ml) as an eluent to remove by-products. Elution with ether (300 ml) produced a pure product. (8.9 g, 46%); m.p. 102°-103° C.; Rf (ether), 0.71; γmax (KBr, cm-1) 3360 (OH), 2940 (C--H), 1200 (Ph), 1040 (C--O), 810 (Ph); δH (400 MHz, CDCl3) 0.91 (67H, m, Me), 1.33 (8H, m), 1.44 (4H, m) 1.80 (4H, m) 4.00 (4H, m), 6.48 (2H, s, OH), 7.09 (1H, s, Ph), 7.36 (ill, s, Ph); t δc (100 MHz, CDCl3) 13.9, 22.5, 25.5, 29.1, 31.4, 69.6, 116.3, 116.4 (PhC--H), 118 (br, C--B), 120.5 (PhC--H), 149.6 (PhC--O), 158.0 (PhC--O).

Provenance & Evidence