1-Chloro-3-iodobenzene → HCID 57493831, compound

HRID 2040861Notes

Reaction equation

HRID 2040861 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[C:13]#[CH:14])[CH3:10]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:14]#[C:13][CH:12]([O:15][CH2:16][CH3:17])[O:11][CH2:9][CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 122691-Chloro-3-iodobenzeneHCID 662853,3-Diethoxypropyne

Product 1

HCID 57493831HCID 57493831, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1-chloro-3-iodobenzene (4 g, 16.8 mmol), propargylaldehyde diethyl acetal (2.66 mL, 18.5 mmol), bis(trifenilphosphine)palladium(II)dichloride (295 mg, 0.42 mmol), cuprous iodide (160 mg, 0.84 mmol) and triethylamine (60 mL) was stirred at r.t. for 3 h. After 4 h, the reaction mixture was quenched with H2O, extracted with EtOAc, which was washed with brine, dried over Na2SO4, and evaporated to dryness in vacuo. The residue was purified by automated flash chromatography (Horizon®TM-Biotage; Petroleum Ether-EtOAc 97:3) to give 4 g of the title compound as a fluid yellowish oil. Yield: 100%.

Workup

  1. waitAfter 4 h
  2. customthe reaction mixture was quenched with H2O
  3. extractionextracted with EtOAc, which
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness in vacuo
  7. customThe residue was purified by automated flash chromatography (Horizon®TM-Biotage; Petroleum Ether-EtOAc 97:3)

Sources & evidence

ORD record
ord-fe2523f367874c3b91265fd972433d10
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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