4-Iodobenzoic acid → HCID 10414477, compound

HRID 2053494Notes

Reaction equation

HRID 2053494 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][O:10][C:11]2[C:20]3[C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:16]([CH3:24])([CH3:23])[C:15]=3[CH:14]=[C:13]([CH:25]([OH:28])[C:26]#[CH:27])[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=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:30]=[CH:29][C:8]([CH2:9][O:10][C:11]2[C:20]3[C:19]([CH3:21])([CH3:22])[CH2:18][CH2:17][C:16]([CH3:23])([CH3:24])[C:15]=3[CH:14]=[C:13]([CH:25]([OH:28])[C:26]#[C:27][C:32]3[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86599548HCID 86599548, compound

Product 1

HCID 10414477HCID 10414477, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner similar to that of Example 1g, by reacting 760 mg (1.9 mmol) of 1-[4-(4-tert-butylbenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]prop-2-yn-1-ol with 390 mg (1.6 mmol) of 4-iodobenzoic acid in the presence of 15 mg of copper iodide and 28 mg of bis(triphenylphosphine)dichloropalladium. The desired product is obtained in the form of white crystals (m=600 mg; yield=71%; m.p.=254° C.).

Sources & evidence

ORD record
ord-a6e555ce88c947f0aafea26f57081f2c
Source dataset
uspto-grants-2008_02
Patent number
US07326803B2

Reaction notes

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