4-Iodobenzoic acid → HCID 69292484, compound

HRID 2053495Notes

Reaction equation

HRID 2053495 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][C:8]2[C:17]3[C:16]([CH3:19])([CH3:18])[CH2:15][CH2:14][C:13]([CH3:21])([CH3:20])[C:12]=3[CH:11]=[C:10]([CH:22]([OH:25])[C:23]#[CH:24])[CH:9]=2)=[CH:4][CH:3]=1.I[C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[C:17]3[C:16]([CH3:18])([CH3:19])[CH2:15][CH2:14][C:13]([CH3:21])([CH3:20])[C:12]=3[CH:11]=[C:10]([CH:22]([OH:25])[C:23]#[C:24][C:29]3[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)[CH:9]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86599550HCID 86599550, compound

Product 1

HCID 69292484HCID 69292484, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner similar to that of Example 1g, by reacting 580 mg (1.6 mmol) of 1-[4-(4-fluorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]prop-2-yn-1-ol with 330 mg (1.3 mmol) of 4-iodobenzoic acid in the presence of 12 mg of copper iodide and 23 mg of bis(triphenylphosphine)dichloropalladium. The desired product is obtained in the form of beige-colored crystals (m=420 mg; yield=67%; m.p. 188° C.).

Sources & evidence

ORD record
ord-3f3a50b180aa4e659abd2e20bb586c8d
Source dataset
uspto-grants-2008_02
Patent number
US07326803B2

Reaction notes

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