Phenyl phosphorus dichloride → 4-Methoxyphenylphenylpyrenylphosphine

Participants

Reaction Steps

Pyrene bromide [IIa] (3.28 g, 15 mmol) was dissolved in 70 mL of THF, and n-BuLi (6.11 mL, 2.7 M, 16.5 mmol, 1.1 eq) was added dropwise to the solution at −78° C. over 15 minutes. The mixture was stirred for 3 hours. This reaction product was dropwise added over 15 minutes to dichlorophenylphosphine [IIIa] (2.03 mL, 15 mmol, 1 eq) dissolved in 6 mL of THF (−78° C.). After stirring overnight, 4-methoxyphenyl magnesium bromide [IVa] (45 mL, 0.5 M, 22.5 mmol, 1.5 eq) was dropwise added over 15 minutes to the reaction mixture at −78° C. After stirring the mixture for 6 hours, the reaction was quenched with 50 mL of saturated ammonium chloride aqueous solution. The inorganic salt produced was removed by suction filtration, followed by extraction with dichloromethane (100 mL×3). The organic layer was dried over sodium sulfate and concentrated on an evaporator. The residue was purified by column chromatography using a developing solvent (dichloromethane:hexane=1:2). The product was obtained as pale yellow crystals in 32% yield. The pale yellow crystals were identified by 1H-NMR, 31P-NMR, 13C-NMR, H—H COSY and C—H COSY.

Provenance & Evidence