Diisopropylamine → HCID 58952506, compound

HRID 597894Notes

Reaction equation

HRID 597894 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1I.C(NC(C)C)(C)C>C(Cl)Cl.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>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 968642,4-Dichloro-1-iodobenzene

Product 1

HCID 58952506HCID 58952506, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-chloro-4-ethynyl-benzene (2.71 g, 0.020 mol), 2,4-dichloro-1-iodo-benzene (3.23 mL, 0.024 mol), PdCl2(PPh3)2 (0.10 g, 1.4 mmol), CuI (1.44 g, 7.6 mmol), and diisopropylamine (7 mL) in DCM (i.e., dichloromethane) (100 mL) was stirred at room temperature for 16 h. The mixture was filtered through CELITE. The filtrate was concentrated in vacuo. The residue was chromatographed (SiO2, hexane) to afford 2,4-dichloro-1-(4-chloro-phenylethynyl)-benzene as a white solid (3.23 g, 87%).

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed (SiO2, hexane)

Sources & evidence

ORD record
ord-b32643887724472682e9edb46a02246a
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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