4-Iodobenzoic acid → HCID 10097988, compound

HRID 735387Notes

Reaction equation

HRID 735387 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[CH:17]=[CH:18][C:19]([CH:27]([OH:30])[C:28]#[CH:29])=[CH:20][C:21]=3[C:22]([CH3:26])([CH3:25])[CH2:23][CH:24]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=1>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.[Cu](I)I>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]3[CH:17]=[CH:18][C:19]([CH:27]([OH:30])[C:28]#[C:29][C:32]4[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=4)=[CH:20][C:21]=3[C:22]([CH3:26])([CH3:25])[CH2:23][CH:24]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86601153HCID 86601153, compound

Product 1

HCID 10097988HCID 10097988, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner similar to that of Example 16b, by reacting 0.28 g (0.71 mmol) of 1-[5-(4-benzyloxyphenyl)-8,8-dimethyl-7,8-dihydro-2-naphthyl]prop-2-yn-1-ol with 0.146 g (0.6 mmol) of 4-iodobenzoic acid, 0.010 g (0.015 mmol) of trans-dichlorobis(triphenylphosphine)palladium and 0.006 g (0.003 mmol) of copper iodide, a yellow solid is obtained (0.03 g; yield=10%; m.p.=171° C.).

Workup

  1. customa yellow solid is obtained (0.03 g; yield=10%; m.p.=171° C.)

Sources & evidence

ORD record
ord-e0a71d125d294edbbdbd7d3133412442
Source dataset
uspto-grants-2009_09
Patent number
US07592478B2

Reaction notes

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