Hydrochloric Acid → Perfluorophenyl 4-bromobutanoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of pentafluorophenol (3.3 g, 17.96 mmol), 4-bromobutanoic acid (3.0 g, 17.96 mmol) and DMAP (0.440 g, 3.59 mmol) in CH2Cl2 (30 ml), cooled to 0° C., EDAC.HCl (5.2 g, 26.94 mmol) was added in portion. The mixture was then stirred at 0° C. for 30 minutes. Then it was gradually warmed to room temperature and stirred for 480 minutes. Then the mixture was diluted with NaH2PO4 aqueous (5%, 50 ml) and acidified with HCl 1N to pH 3-4. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (2×50 ml). The organic phase washed with brine, dried over Na2SO4 and evaporated to give an oil that was purified by flash chromatography (n-Hexane/EtOAc 98:2) to yield 4-bromobutanoic acid pentafluorophenyl ester (5.2 g, 86%) as a colorless oil.

Provenance & Evidence