4-Iodobenzoic acid → HCID 10389172, compound

HRID 2377212Notes

Reaction equation

HRID 2377212 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([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)(C)(C)C.I[C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=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:28][CH:25]([C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH3:1])=[CH:10][CH:9]=2)[C:20]2[C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:16]([CH3:24])([CH3:23])[C:15]=2[CH:14]=1)[C:26]#[C:27][C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86598703HCID 86598703, compound

Product 1

HCID 10389172HCID 10389172, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a similar manner to that of Example 1g, by reacting 300 mg (0.8 mmol) of 1-[4-(4-tert-butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]prop-2-yn-1-ol with 166 mg (0.7 mmol) of 4-iodobenzoic acid in the presence of 7 mg of copper iodide and 12 mg of bis(triphenylphosphine)dichloropalladium. The desired product is obtained in the form of white crystals (m=280 mg; yield=72%; m.p.=180° C.).

Sources & evidence

ORD record
ord-017500e8e655469c8c81efcc4fda1f80
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

Loading…