N-bromobutanimide → HCID 178442369, compound

Participants

Reaction Steps

To a flask containing 1.00 g (1.25 mmol) of 5,15-bis(3,5-dihexylphenyl)porphyrin and 200 mL of chloroform was added 223 mg (1.25 mmol) of N-bromosuccinimide (NBS). After stirring the reaction mixture for 15 min, TLC (hexanes/methylene chloride, 2:1) indicated that the product was present together with lesser amounts of the starting material and the dibrominated porphyrin. The reaction mixture was concentrated to a viscous oil and this material was chromatographed on silica gel (hexanes/methylene chloride, 4:1/3:1) to give 1.116 g (68% yield) of the desired product. 1H NMR (400 MHz) δ−2.97 (2H, s, —NH), 0.93 (12H, t, J=7 Hz, —CH3), 1.36-1.44 (16H, m, —CH2—), 1.48-1.56 (8H, m, —CH2—), 1.83-1.91 (8H, m, —CH2—), 2.89 (8H, t, J=8 Hz, —CH2—), 7.43 (2H, s, Ar—H), 7.85 (4H, s, Ar—H), 8.99 (2H, d, J=4 Hz, β-H), 9.00 (2H, d, J=4 Hz, β-H), 9.28 (2H, d, J=4 Hz, β-H), 9.73 (2H, d, J=5 Hz, β-H), 10.16 (1H, s, meso-H); MALDI-TOF-MS m/z calcd. for C56H69N4Br 876.5, obsd. 876.4; UV/vis (CH2Cl2) 416, 512, 547, 588, 645 (nm).

Provenance & Evidence