4-Iodobenzoic acid → HCID 10389172, compound

HRID 2377209Notes

Reaction equation

HRID 2377209 reaction equation
[CH3:1][C:2]1([CH3:25])[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]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[C:3]1=2.I[C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=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]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C:3]2[C:2]([CH3:25])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)[C:15]#[C:16][C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86598701HCID 86598701, compound

Product 1

HCID 10389172HCID 10389172, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a similar manner to that of Example 1g, by reacting 950 mg (2.9 mmol) of 1-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)prop-2-yn-1-ol with 595 mg (2.4 mmol) of 4-iodobenzoic acid in the presence of 47 mg of copper iodide and 54 mg of bis(triphenylphosphine)dichloropalladium. The desired product is obtained in the form of white crystals (m=1 g; yield=81%; m.p.=207° C.).

Sources & evidence

ORD record
ord-5c9ac9abe77a4cd7b3fa6e2f07f7d36a
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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