Iodine → HCID 13259985, compound

HRID 569200Notes

Reaction equation

HRID 569200 reaction equation
[Al].II.[CH2:4](Br)[C:5]#[CH:6].[Cl:8][C:9]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:10]=1[O:11][CH2:12][CH2:13][C:14]([CH3:24])([CH3:23])[C:15](=[O:22])[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1.[Cl-].[NH4+]>O1CCCC1.[Hg](Cl)Cl>[Cl:8][C:9]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:10]=1[O:11][CH2:12][CH2:13][C:14]([CH3:24])([CH3:23])[C:15]([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)([OH:22])[CH2:6][C:5]#[CH:4]

Participants

8

Reactant 5

HCID 807IodineHCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 5359268AluminumHCID 13259981HCID 13259981, compound

Product 1

HCID 13259985HCID 13259985, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-60 °C

Procedure

1.58 g (0.058 mol) of aluminum (in the form of flakes) are covered with 7.3 ml of tetrahydrofuran, and a catalytic amount (0.05 g) of mercury(II) chloride and one iodine crystal are added. After standing at 20° C. for 12 hours, 10.3 g (0.087 mol) of propargyl bromide in 11 ml of tetrahydrofuran are added dropwise at 60° C. The mixture is then cooled down to -60° C. and a solution of 17.1 g (0.05 mol) of 5-(2,4-dichlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-pentanone in 20 ml of tetrahydrofuran is added dropwise. The temperature is allowed to rise to 0° C., this temperature is maintained for a further hour and 22 ml of a saturated aqueous solution of ammonium chloride are added. The mixture is then filtered, the filtrate is evaporated in vacuo and the residue is taken up in 200 ml of ethyl acetate. After washing three times with 100 ml of water each time, the organic phase is dried over sodium sulphate and then evaporated in vacuo. Solvent residues are removed at 50° C. and 0.01 mbar. 14.3 g (74.8% of theory) of 7-(2,4-dichlorophenoxy)-5,5-dimethyl-4-(1,2,4-triazol-1-ylmethyl)-1-heptin-4-ol are obtained as a brownish oil of refractive index nD20 =1.5642.

Workup

  1. customto rise to 0° C.
  2. temperaturethis temperature is maintained for a further hour
  3. filtrationThe mixture is then filtered
  4. customthe filtrate is evaporated in vacuo
  5. washAfter washing three times with 100 ml of water each time
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. customevaporated in vacuo
  8. customSolvent residues are removed at 50° C.

Sources & evidence

ORD record
ord-680b45499cac41e3b3e38b46a8512b08
Source dataset
uspto-grants-1988_03
Patent number
US04731452

Reaction notes

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