4-Iodobenzoic acid → HCID 25109556, compound

HRID 1698402Notes

Reaction equation

HRID 1698402 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]([OH:17])[C:15]#[CH:16])[CH:8]=[CH:9][C:10]=1[N:11]([CH3:13])[CH3:12])([CH3:4])([CH3:3])[CH3:2].I[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1>[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:14]([OH:17])[C:15]#[C:16][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH3:12])[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 866465671-(3-Tert-butyl-4-dimethylaminophenyl)prop-2-yn-1-ol

Product 1

HCID 25109556HCID 25109556, compoundYield 62.2%

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 900 mg (3.8 mmol) of 1-(3-tert-butyl-4-dimethylaminophenyl)prop-2-yn-1-ol with 805 mg (3.2 mmol) of 4-iodobenzoic acid, 30 mg (0.16 mmol) of copper iodide and 56 mg (0.08 mmol) of bis(triphenylphosphine)palladium chloride. 700 mg of 4-[3-(3-tert-butyl-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]benzoic acid are obtained in the form of a beige solid (Mp=139° C., yield=64%).

Sources & evidence

ORD record
ord-dc4ea14e93074c0a83367e2e3087dc18
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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