1-Chloro-3-iodobenzene → HCID 19605228, compound

HRID 1603634Notes

Reaction equation

HRID 1603634 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[CH2:9]([OH:15])[CH2:10][CH2:11][CH2:12][C:13]#[CH:14]>C(N(CC)CC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:13][CH2:12][CH2:11][C:10]#[C:9][OH:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 122691-Chloro-3-iodobenzeneHCID 702345-Hexyn-1-ol

Product 1

HCID 19605228HCID 19605228, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of 3-chloroiodobenzene (14.3 g, 60 mmol), tetrakis(triphenylphosphine) palladium (2.1 g, 1.8 mmol) and 5-hexyn-1-ol (5.9 g, 60 mmol) in triethylamine (120 ml) was stirred at 25° C. for 3 h and partitioned between water and ether. The ether layer was separated and the aqueous extracted with ether. The combined either extracts were washed with 1N HCl and dried (Na2SO4). The ether was evaporated and the residue purified by flash chromatography on silica using dichloromethane as eluant. Evaporation of the appropriate fractions gave the product as an oil (11.5 g 92%)

Workup

  1. custompartitioned between water and ether
  2. customThe ether layer was separated
  3. extractionthe aqueous extracted with ether
  4. washextracts were washed with 1N HCl
  5. dry with materialdried (Na2SO4)
  6. customThe ether was evaporated
  7. customthe residue purified by flash chromatography on silica
  8. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-8b7519a828874fc0b788ced18e71ef66
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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