Ethyl Acetate → 5,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrin

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Reaction Steps

To a solution of porphyrin 1 (400 mg, 0.47 mmol) in dry dichloromethane (25 mL) at −20° C. was added BBr3 (451 μL, 4.68 mmol). The resulting green solution was stirred for 12 hours at room temperature, then placed in ice water, ethyl acetate was added to the suspension and the mixture was washed with NaHCO3. The organic layer was separated, washed twice with water and then dried over anhydrous Na2SO4. The resulting solution was evaporated. The residue was purified by column chromatography (silica gel, 20:1 ethyl acetate/methanol) to yield porphyrin 2 as a purple powder (300 mg, 87%). 1H NMR (400 MHz, MeOD): δ 8.81 (s, 8H), 7.38 (t, J=8 Hz, 4H), 6.72 (d, J=8 Hz, 8H). HRESI-MS ([M+H]+) calcd for C44H31N4O8 743.2436, found 743.2136.

Provenance & Evidence