Potassium Carbonate → 1-Ethynyl-4-iodobenzene

HRID 18349Notes

Reaction equation

HRID 18349 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)#[CH:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11808725(4-Iodophenylethynyl)trimethylsilane

Product 1

HCID 121608331-Ethynyl-4-iodobenzeneYield 64.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ((4-iodophenyl)ethynyl)trimethylsilane (5) (2.07 g, 6.23 mmol) in methanol (40 mL) was added K2CO3 (8.0 g, 57.9 mmol) and the reaction was allowed to stir for 48 hours. The volatiles were then removed in vacuo and the residue partitioned between ethyl acetate and H2O. The layers were separated and the aqueous phase re-extracted with ethyl acetate (2×). The combined organic layers were washed (H2O, brine), dried (Na2SO4), and filtered. The solvent was removed in vacuo and the residue was crystallized from hexane at −20° C. (in 2 crops) to give 1-ethynyl-4-iodobenzene (6) as a colorless solid (0.92 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ 7.66 (app d, J=8.6 Hz, 2H), 7.20 (app d, J=8.5 Hz, 2H), 1.54 (s, 1H).

Workup

  1. customThe volatiles were then removed in vacuo
  2. customthe residue partitioned between ethyl acetate and H2O
  3. customThe layers were separated
  4. extractionthe aqueous phase re-extracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed (H2O, brine)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customthe residue was crystallized from hexane at −20° C. (in 2 crops)

Sources & evidence

ORD record
ord-b4dda8d4d4954a57bf5cb0599e52ff3b
Source dataset
uspto-grants-2010_06
Patent number
US07741347B2

Reaction notes

Loading…