Potassium Carbonate → HCID 102326582, compound

Participants

Reaction Conditions

Reaction Steps

A synthesis of was published in Hargadon, M. T.; Davey, E. A.; McIntyre, T. B.; Gnanamgari, D.; Wynne, C. M.; Swift, R. C.; Zimbalist, J. R.; Fredericks, B. L.; Nicastro, A. J.; Goodson, F. E. Macromolecules 2008, 41, 741-750. A 250 mL round-bottomed flask was charged with 5.41 g (9.14 mmol) of hexaethylene glycol di(p-toluenesulfonate), 4.67 g (27.0 mmol) of 3-bromophenol, 12.8 g of K2CO3 (92.6 mmol), and 50 mL of DMF. The reaction was then left to stir overnight in a 60° C. oil bath, after which the solvent was removed via vacuum distillation. Dichloromethane was then added to the residue, and the resulting suspension was filtered to remove excess carbonate and salt byproducts. Afterwards, the solvent was removed with a rotary evaporator, and the residue was heated in a kugelrohr oven under a dynamic 5 mtorr vacuum to remove excess 3-bromophenol. The crude product was then chromatographed on silica with an eluent of hexanes/EtOAc adjusted to give an Rf for the product of 0.2-0.3. Hexaethylene glycol di(3-bromophenyl)ether (3.70 g, 6.26 mmol, 69% yield), was then isolated as a pale yellow oil after distillation at 200° C. (<1 mtorr): 1H NMR (300 MHz, CDCl3) δ 7.05-7.15 (multiple resonances, 6H); 6.84 (dm, Jd=8.1 Hz, 2H); 4.09 (t, J=4.5 Hz, 4H); 3.83 (t, J=4.8 Hz, 4H); 3.64-3.74 (multiple resonances, 8H); 3.65 (s, 8H); 13C NMR (75 MHz, CDCl3) δ 159.7, 130.4, 124.0, 122.7, 118.3, 113.8, 70.9, 70.7, 70.6, 69.6, 67.9, (one signal not resolved). Anal. Calcd. for C24H32Br2O7: C, 48.67; H, 5.44; Found: C, 48.83; H, 5.59.

Provenance & Evidence