4-Iodobenzoic acid → HCID 69292517, compound

HRID 2053493Notes

Reaction equation

HRID 2053493 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([OH:17])[C:15]#[CH:16])[CH:5]=[C:4]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[C:3]1=2.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>[OH:17][CH:14]([C:6]1[CH:5]=[C:4]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:3]2[C:2]([CH3:27])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)[C:15]#[C:16][C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86599546HCID 86599546, compound

Product 1

HCID 69292517HCID 69292517, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner similar to that of Example 1g, by reacting 1.22 g (3.3 mmol) of 1-[5,5,8,8-tetramethyl-4-(4-methylbenzyloxy)-5,6,7,8-tetrahydro-2-naphthyl]prop-2-yn-1-ol with 680 mg (2.8 mmol) of 4-iodobenzoic acid in the presence of 27 mg of copper iodide and 49 mg of bis(triphenylphosphine)dichloropalladium. The desired product is obtained in the form of beige-colored crystals (m=900 mg; yield=67%; m.p.=219° C.).

Sources & evidence

ORD record
ord-48aebd18479741b7a0bbddc762b229d4
Source dataset
uspto-grants-2008_02
Patent number
US07326803B2

Reaction notes

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