4-Iodobenzoic acid → 4-[3-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]benzoic acid

HRID 1698415Notes

Reaction equation

HRID 1698415 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([C:15]1[CH:16]=[C:17]([CH:25]([OH:28])[C:26]#[CH:27])[CH:18]=[C:19]([Cl:24])[C:20]=1[N:21]([CH3:23])[CH3:22])([CH3:14])([CH3:13])[CH3:12]>[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:11]([C:15]1[CH:16]=[C:17]([CH:25]([OH:28])[C:26]#[C:27][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:18]=[C:19]([Cl:24])[C:20]=1[N:21]([CH3:22])[CH3:23])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 866465721-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)prop-2-yn-1-ol

Product 1

HCID 251095604-[3-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]benzoic acidYield 87.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner analogous to example 1 f, the process is carried out by a reaction of 200 mg (0.8 mmol) of 4-iodobenzoic acid with 300 mg (1.1 mmol) of 1-(3-tert-butyl-5-chloro-4-dimethylaminophenyl)prop-2-yn-1-ol in the presence of 8 mg (0.04 mmol) of copper iodide and 16 mg (0.02 mmol) of bis(triphenylphosphine)palladium chloride. 270 mg of 4-[3-(3-tert-butyl-5-chloro-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]benzoic acid are obtained in the form of a whitish solid (Mp=120° C., yield=87%).

Sources & evidence

ORD record
ord-69144b5147ea451382d5b384f9f645f7
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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