p-Diiodobenzene → HCID 178435658, compound

HRID 2111466Notes

Reaction equation

HRID 2111466 reaction equation
[CH2:1]([C-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1)[CH3:2].[C:8]([C-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)#[CH:9].[Fe+2:15].[I:16][C:17]1[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=1>C1COCC1.CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:1]([C-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1)[CH3:2].[I:16][C:17]1[CH:22]=[CH:21][C:20]([C:9]#[C:8][C-:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)=[CH:19][CH:18]=1.[Fe+2:15]

Participants

7

Reactant 2

HCID 12208p-DiiodobenzeneHCID 178435656HCID 178435656, compound

Product 1

HCID 178435658HCID 178435658, compoundYield 97.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

Following the procedure for preparing 6, samples of 13 (1.0 g, 4.2 mmol), 1,4-diiodobenzene (2.8 g, 8.5 mmol), PdCl2(PPh3)2 (30 mg, 43 μmol) and CuI (5.0 mg, 26 μmol) were reacted in THF (20 mL) and Et3N (20 mL). The reaction mixture was stirred at 50° C. for 5 h and worked up. The resulting residue was purified by column chromatography (silica, petroleum ether) to afford 1.8 g (95%) of a red-brown solid. mp 55-57° C.; 1H NMR δ 1.17 (t, J=7.5 Hz, 3H), 2.35 (q, J=7.5 Hz, 2H), 4.10 (s, 4H), 4.18 (t, J=2.1 Hz, 2H), 4.40 (t, J=2.1 Hz, 2H), 7.18, 7.64 (AA′BB′, J=8.1 Hz, 2×2H); 13C NMR δ 15.5, 22.3, 67.0, 68.9, 69.5, 70.2, 74. 5, 91.2, 123.3, 133.5, 134.0, 135.8; FAB-MS obsd 439.8721, calcd exact mass 439.8724 (C20H17FeI).

Workup

  1. customThe resulting residue was purified by column chromatography (silica, petroleum ether)

Sources & evidence

ORD record
ord-41221b142c224580abf5c4d70bb728bf
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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