Iodine → HCID 13259983, compound

HRID 2166356Notes

Reaction equation

HRID 2166356 reaction equation
II.[Al].[CH2:4](Br)[C:5]#[CH:6].[CH:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[C:10]([C:16]([CH2:18][Cl:19])=[O:17])[CH:9]=1.[Cl-].[NH4+]>O1CCCC1.[Hg](Cl)Cl>[Cl:19][CH2:18][C:16]([C:10]1[CH:9]=[CH:8][C:13]([Cl:14])=[CH:12][C:11]=1[Cl:15])([OH:17])[CH2:6][C:5]#[CH:4]

Participants

8

Reactant 5

HCID 807IodineHCID 7842Propargyl bromideHCID 202502,2',4'-TrichloroacetophenoneHCID 25517Ammonium ChlorideHCID 5359268Aluminum

Product 1

HCID 13259983HCID 13259983, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A pinch of mercury(II) chloride and an iodine crystal are added to 13 g (0.48 mol) of aluminum (in the form of flakes), the substances are covered with a layer of 60 ml of tetrahydrofuran and the mixture is stirred for 10 hours at 20° C. The mixture is then warmed to 60° C., and a solution of 84.5 g (0.71 mol) of propargyl bromide in 85 ml of tetrahydrofuran is added dropwise. The mixture is then cooled to -60° C., and a solution of 111.7 g (0.5 mol) of ω-chloro-2,4-dichloroacetophenone in 165 ml of tetrahydrofuran is added dropwise. The mixture is allowed to warm up to 0° C., and after 1 hour hydrolysis is effected with 170 ml of saturated, aqueous ammonium chloride solution. Thereafter, the mixture is filtered, the filtrate is evaporated down in vacuo and 500 ml of ethyl acetate are added to the residue. The organic phase is separated off, washed with three times 300 ml of water and dried over anhydrous sodium sulphate, and the solvent is distilled off under reduced pressure. 113.5 g (86.1% of theory) of 5-chloro-4-(2,4-dichlorophenyl)-pent-1-in-4-ol are obtained as colorless crystals of melting point 55°-57° C.

Workup

  1. temperatureThe mixture is then warmed to 60° C.
  2. temperatureThe mixture is then cooled to -60° C.
  3. temperatureto warm up to 0° C.
  4. customafter 1 hour hydrolysis
  5. filtrationThereafter, the mixture is filtered
  6. customthe filtrate is evaporated down in vacuo and 500 ml of ethyl acetate
  7. additionare added to the residue
  8. customThe organic phase is separated off
  9. washwashed with three times 300 ml of water
  10. dry with materialdried over anhydrous sodium sulphate
  11. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-6eb2e5d35b5a4f39989d2c3182d6d354
Source dataset
uspto-grants-1990_07
Patent number
US04945101

Reaction notes

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