Benzene, 1-bromo-3-iodo- → HCID 178419389, compound

Participants

Reaction Steps

1-(Ferrocenylethynyl)-3-bromobenzene 204 was prepared following the general procedure found in General Procedure for the Palladium-Catalyzed Cross-Coupling Reactions using 500 mg (2.38 mmol) of ethynylferrocene 200, 642 mg (2.27 mmol) of 1-bromo-3-iodobenzene 202, 25.5 mg (0.114 mmol) Pd(OAc)2, 89.2 mg (0.341 mmol) of PPh3, and 10.8 mg (0.0568 mmol) of CuI in 25 mL tetrahydrofuran, 5 mL pyridine and 5 mL diisopropylamine at 25° C. The residue was purified using a 5:1 hexane/CH2Cl2 solvent mixture to afford 761 mg (92%) of an orange-red solid, m.p. 130° C. Spectral data for 1-(ferrocenylethynyl)-3-bromobenzene 204: IR (cm−1, KBr): 3094 (C—H), 3057 (C—H), 2218 (C° C.), 2204 (C≡C), 1591 (C═C, benzene), 1583 (C═C, benzene), 1552 (C═C, benzene), 1411 (C═C, ferrocene). H NMR (d in CDCl3): 7.63 (t, J=1.7 Hz, 1H), 7.41 (m, 2H), 7.17 (t, J=7.8 Hz, 1H), 4.50 (t, J=1.9 Hz, 2H), 4.25 (t, J=1.9 Hz, 2H), 4.24 (s, 5H). Analysis for 1-(ferrocenylethynyl)-3-bromobenzene 204 (C18H13FeBr) Calcd: C, 59.22%; H, 3.59%. Found: C, 59.15%; H, 3.84%.

Provenance & Evidence