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

HRID 1838704Notes

Reaction equation

HRID 1838704 reaction equation
[C:1]([C-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1)#[CH:2].[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1.N1C=CC=CC=1.C(NC(C)C)(C)C.[Pd].CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[C-:3]1([C:1]#[C:2][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([Br:14])[CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13]

Participants

10

Reactant 3

HCID 11561Benzene, 1-bromo-3-iodo-HCID 11776TriphenylphosphineHCID 15188896HCID 15188896, compound

Product 1

HCID 178419389HCID 178419389, compound

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 1049PyridineSolventHCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

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%.

Workup

  1. customat 25° C
  2. customThe residue was purified

Sources & evidence

ORD record
ord-bda702db1da14887a42125e646c6d719
Source dataset
uspto-grants-2004_01
Patent number
US06673953B2

Reaction notes

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