Iodine → HCID 13259985, compound

HRID 2166351Notes

Reaction equation

HRID 2166351 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 a layer of 7.3 ml of tetrahydrofuran, and a catalytic amount (0.05 g) of mercury(II) chloride and an iodine crystal are added. After the mixture has stood for 12 hours at 20° C., 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 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)-pentan-2-one in 20 ml of tetrahydrofuran is added dropwise. The mixture is allowed to warm up to 0° C. and is kept for a further hour at this temperature, and 22 ml of a saturated, aqueous ammonium chloride solution are added. Thereafter, the mixture is filtered, the filtrate is evaporated down in vacuo and the residue is taken up in 200 ml of ethyl acetate. After the solution has been washed with three times 100 ml of water, the organic phase is dried over sodium sulphate and then evaporated down in vacuo. Residues of solvent 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-yl-methyl)-hept-1-in-4-ol are obtained as a brownish oil of refractive index nD20 =1.5642.

Workup

  1. temperatureto warm up to 0° C.
  2. waitis kept for a further hour at this temperature, and 22 ml
  3. filtrationThereafter, the mixture is filtered
  4. customthe filtrate is evaporated down in vacuo
  5. washAfter the solution has been washed with three times 100 ml of water
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. customevaporated down in vacuo
  8. customResidues of solvent are removed at 50° C.

Sources & evidence

ORD record
ord-379a82bc25364632b4f762459c6eaf8b
Source dataset
uspto-grants-1990_07
Patent number
US04945101

Reaction notes

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