Toluene → 5'-(4-(Bis(4-methoxyphenyl)amino)phenyl)-3,4'-dihexyl-2,2'-bithiophen-5-yl(butyl)phosphinic acid

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Reaction Conditions

Reaction Steps

The 5′-(4-(bis(4-methoxyphenyl)amino)phenyl)-3,4′-dihexyl-2,2′-bithiophen-5-yl(butyl)phosphinic acid was prepared applying a modified procedure of Y. Xu et al., Synthesis, 1984, 778. 4-(5′-Bromo-3′,4-dihexyl-2,2′-bithiophen-5-yl)-N,N-bis(4-methoxyphenyl)aniline (216 mg, 0.8 mmol) was placed in a Schlenck tube, and toluene (0.2 ml), ethyl butylphosphinate (152 mg, 0.88 mmol), triethylamine (0.36 ml, 2.6 mmol), and tetrakis[triphenylphosphine]palladium (46.2 mg, 0.04 mmol) was added under a stream of argon, stoppered, and heated in an oil bath at 110° C. for 10 h. After the mixture has been cooled, ethyl acetate (5 ml) is added and the solid is removed by filtration. The filtrate is concentrated on a rotatory evaporator and the residue is purified by column chromatography on silica gel eluting with petroleum ether (bp. 60-90° C.)/ethyl acetate. The ester thus obtained was hydrolised with 12% aqueous HCl (2×2 mL) evaporating to dryness on a waterbath yielding 5′-(4-(bis(4-methoxyphenyl)amino)phenyl)-3,4′-dihexyl-2,2′-bithiophen-5-yl(butyl)phosphinic acid (190 mg, 82%).

Provenance & Evidence