Diisopropylamine → HCID 2185393, compound

HRID 330820Notes

Reaction equation

HRID 330820 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH3:2].[Br:12][C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1.C(NC(C)C)(C)C.CCOC(C)=O>C1COCC1.[Cu]I>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 115221-Bromo-4-iodobenzeneHCID 27751241-Ethoxy-4-ethynylbenzene

Product 1

HCID 2185393HCID 2185393, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 1.60 g (11.0 mmol) 4-ethoxyphenylacetylene in 40 mL THF are added 3.10 g (11.0 mmol) 1-bromo-4-iodo-benzene under argon, followed by 0.18 g (0.22 mmol) Pd(dppf)Cl2CH2Cl2 as catalyst, 0.04 g (0.22 mmol) copper(I)iodide and 3.10 mL (21.9 mmol) diisopropylamine as base. The mixture is stirred at rt for 3 h. After that time, EtOAc is added and the organic layer is washed with ammonia (5%, 2×) and water (1×). The organic layer is separated, dried over magnesium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silicia gel; PE:EtOAc 9:1) to yield the desired product.

Workup

  1. washthe organic layer is washed with ammonia (5%, 2×) and water (1×)
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent is evaporated
  5. customThe residue is purified by column chromatography (silicia gel; PE:EtOAc 9:1)

Sources & evidence

ORD record
ord-e5a57b4e3971496cb2b74432d00a128d
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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