Diisopropylamine → HCID 23006387, compound

HRID 597884Notes

Reaction equation

HRID 597884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH3:9][CH:10]([OH:13])[C:11]#[CH:12].N(C(C)C)C(C)C>ClCCl.[Cu]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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]#[C:11][CH:10]([OH:13])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 125101-Chloro-4-iodobenzeneHCID 162393-Butyn-2-ol

Product 1

HCID 23006387HCID 23006387, compoundYield 100.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 4-chloro iodobenzene (10 g, 42 mmol), 3-butyn-2-ol (6.6 mL, 84 mmol, 2 eq.), and iPr2NH (14.8 mL, 105 mmol, 2.5 eq.) in 200 mL dichloromethane was added CuI (1.6 g, 8.4 mmol, 0.2 eq.) followed by Pd(PPh3)2Cl2 (1.5 g, 2.1 mmol, 5 mol %). The mixture was stirred for 1.5 hr at room temperature, concentrated and diluted with ether. The insoluble components of the mixture were filtered off and the filtrate washed with 1N HCl and brine, dried over MgSO4, filtered, concentrated and chromatographed with 20% ethyl acetate-hexane to provide 7.6 g of 4-(4-chloro-phenyl)-but-3-yn-2-ol.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ether
  3. filtrationThe insoluble components of the mixture were filtered off
  4. washthe filtrate washed with 1N HCl and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed with 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-001fb85875b74a8abadb62d89f040a8d
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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