Triphenylphosphine → (3,5-Dichloro-4-formylphenoxymethyl)-phosphonic acid diethyl ester

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Reaction Steps

To a solution of 2,6-dichloro-4-hydroxy-benzaldehyde (190 mg, 1.0 mmol) and hydroxymethyl-phosphonic acid diethyl ester (278 mg, 1.0 mmol) in THF (8 mL) was added PPh3-resin (553 mg, 2.13 mmol/g) and DEAD (0.54 ml of 40% solution, 1.2 mmol). The suspension was stirred at ambient temperature overnight then the reaction mixture was filtered and partioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (1:3) gave (3,5-dichloro-4-formylphenoxymethyl)-phosphonic acid diethyl ester as a colorless oil.

Provenance & Evidence