1-Iodo-4-propylbenzene → 3-(4-Propylphenyl)-furan

HRID 566752Notes

Reaction equation

HRID 566752 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10]N=[CH:8][CH:7]=2)=[CH:2]1.I[C:13]1[CH:18]=CC(CCC)=[CH:15][CH:14]=1.O1C=CC(B(O)O)=C1>>[CH2:13]([C:18]1[CH:10]=[CH:11][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[CH:7][CH:8]=1)[CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 6125411-Iodo-4-propylbenzeneHCID 2734358Furan-3-boronic acidHCID 108556024-(Furan-3-yl)pyridine

Product 1

HCID 183804433-(4-Propylphenyl)-furan

Procedure

As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz).

Workup

  1. customto furnish

Sources & evidence

ORD record
ord-3c4a0e6ab905422fbf010626880be75e
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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