Methyl 4-iodosalicylate → HCID 67276336, compound

HRID 1698410Notes

Reaction equation

HRID 1698410 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:19])[C:17]#[CH:18])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].I[C:21]1[CH:22]=[C:23]([OH:31])[C:24](=[CH:29][CH:30]=1)[C:25]([O:27][CH3:28])=[O:26]>[Cu](I)I.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>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:19])[C:17]#[C:18][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([OH:31])[CH:22]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 11380407Methyl 4-iodosalicylateHCID 86646563HCID 86646563, compound

Product 1

HCID 67276336HCID 67276336, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 3.7 g (15 mmol) of 1-(3-tert-butyl-4-diethylaminophenyl)prop-2-yn-1-ol with 3.3 g (12 mmol) of methyl 4-iodosalicylate, 114 mg (0.6 mmol) of copper iodide and 210 mg (0.3 mmol) of bis(triphenylphosphine)palladium chloride. 4 g of methyl 4-[3-(3-tert-butyl-4-diethylaminophenyl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoate are obtained in the form of yellow oil (yield=66%).

Sources & evidence

ORD record
ord-22504eff2348478187e78bfee5f31585
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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