3,5-Dichloro-2-iodophenol → (5-Propylbenzofuran-2-yl)methanol

HRID 710482Notes

Reaction equation

HRID 710482 reaction equation
I[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[OH:11].Cl[C:13]1[C:14](I)=[C:15]([OH:20])C=C(Cl)C=1>>[CH2:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:14]([CH2:15][OH:20])=[CH:13][C:2]=2[CH:7]=1)[CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 401517703,5-Dichloro-2-iodophenolHCID 667268552-Iodo-4-propylphenol

Product 1

HCID 65440135(5-Propylbenzofuran-2-yl)methanol

Procedure

When the product of Step A was substituted for 3,5-dichloro-2-iodophenol in Example 8, Step E, the similar process afforded the title compound in 31%, as off-white oil. 1H-NMR (CDCl3) 0.93 (m, 3H); 1.58-1.73 (m, 2H); 1.9 (tr, 1H, J=6 Hz); 2.65 (tr, 2H, J=6 Hz); 4.76 (d, 2H, J=6 Hz); 6.58 (s, 1H); 7.08 (dd, 1H, J=3, 9 Hz); 7.3-7.37 (m, 2H).

Sources & evidence

ORD record
ord-fac39ac3a9d842879724f06a39e577e4
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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