Benzoic acid, 2,5-diiodo- → HCID 11089200, compound

HRID 2186410Notes

Reaction equation

HRID 2186410 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>[Cu]I>[I:1][C:2]1[CH:10]=[CH:9][C:8]([C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 26549Benzoic acid, 2,5-diiodo-HCID 66111Trimethylsilylacetylene

Product 1

HCID 11089200HCID 11089200, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

1.12 g of 2,5-diiodobenzoic acid (3 mmol, 1 eq.), 210 mg of dichlorobis-triphenylphosphinepalladium(II) (0.3 mmol, 0.1 eq.) and 200 mg of copper(I) iodide (1 mmol, 0.34 eq.) are dissolved in 60 ml of a THF/TEA mixture (3/1). After the addition of 425 μl of trimethylsilylacetylene (3 mmol, 1 eq.), stirring is continued at room temperature for 16 hours in the dark. The reaction medium is then evaporated to dryness and the residue obtained is purified by flash chromatography on silica 60H (hexane/EtOAc/AcOH: 70/30/1%) to give 754 mg of 2-iodo-5-trimethylsilylethynylbenzoic acid in the form of fine yellow needles after drying under vacuum (yield: 73%).

Workup

  1. customThe reaction medium is then evaporated to dryness
  2. customthe residue obtained
  3. customis purified by flash chromatography on silica 60H (hexane/EtOAc/AcOH: 70/30/1%)

Sources & evidence

ORD record
ord-a6c2d22d593747fdb6f6fb894f0f7db8
Source dataset
uspto-grants-2002_06
Patent number
US06403705B1

Reaction notes

Loading…