1,3-Bis(diphenylphosphino)propane → 4-{3-[(Ethyloxy)(methyl)phosphoryl]propanoyl}benzoic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl [3-(4-bromophenyl)-3-oxopropyl]methylphosphinate (3 g, 9.40 mmol), palladium(II) acetate (0.106 g, 0.470 mmol) and 1,3-bis(diphenylphosphino)propane (0.194 g, 0.470 mmol) were taken up in DMF (24 mL)/water (8 mL). CO was bubbled through for 10 minutes before adding DIPEA (3.28 mL, 18.80 mmol) and stirring at 70° C. under a balloon of CO overnight. Room temperature was attained and saturated NaHCO3 was added. The aqueous phase was extracted with EtOAc (×2) before acidifying with 2N HCl and extracting again with EtOAc (×2). The combined organic extracts from the acidic aqueous were washed with brine, dried over MgSO4 and concentrated in vacuo to give 4-{3-[(ethyloxy)(methyl)phosphoryl]propanoyl}benzoic acid as a pale yellow solid.

Provenance & Evidence