Diisopropylamine → 4-(3,5-Dichloro-phenyl)-3-butyn-2-one

HRID 413935

Reaction equation

HRID 413935 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[CH3:10][C:11](=[O:14])[C:12]#[CH:13].C(NC(C)C)(C)C>C1COCC1.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>[Cl:1][C:2]1[CH:7]=[C:6]([C:13]#[C:12][C:11](=[O:14])[CH3:10])[CH:5]=[C:4]([Cl:9])[CH:3]=1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 15018Butyn-2-oneHCID 764241,3-Dichloro-5-iodobenzene

Product 1

HCID 185224514-(3,5-Dichloro-phenyl)-3-butyn-2-one

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,3-dichloro-5-iodo-benzene (3.44 g, 12.6 mmol) in THF (220 mL) was added PdCl2(PPh3)2 (904 mg, 1.29 mmol), 3-butyn-2-one (2.18 g, 32.0 mmol), copper(l)iodide (380 mg, 2 mmol) and diisopropylamine (44 mL). The reaction mixture was stirred at room temperature for 48 hours, filtered and evaporated. The residue was purified by column chromatography using methylene chloride:hexanes (1:1) as eluent. The desired 4-(3,5-dichloro-phenyl)-3-butyn-2-one product was isolated in 977 mg yield.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-460b9aa8d211412dbde382390db9e230
Source dataset
uspto-grants-2003_05
Patent number
US06569901B2

Linked notes

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