Iodine → HCID 22768559, compound

HRID 1764540Notes

Reaction equation

HRID 1764540 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.II.[Mg].C(O[Si:16]([O:19][CH2:20][CH2:21][CH3:22])([CH3:18])[CH3:17])CC>O1CCCC1>[CH2:20]([O:19][Si:16]([CH3:17])([CH3:18])[C:2]1[CH:7]=[CH:6][C:5]([Si:16]([O:19][CH2:20][CH2:21][CH3:22])([CH3:18])[CH3:17])=[CH:4][CH:3]=1)[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 807IodineHCID 46851,4-DichlorobenzeneHCID 525753DimethyldipropoxysilaneHCID 5462224Magnesium

Product 1

HCID 22768559HCID 22768559, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
132 °C

Procedure

Magnesium turnings (478 g, 19.7 m) in a 12 l, flask were dried as described in Example II. The reactant stock solution was prepared by dissolving 1400 g (9.7m) of para-dichlorobenzene in 3700 g (21m) of di-n-propoxydimethylsilane and 515 g (7.2 m) of tetrahydrofuran. Fresh cuprous chloride (10.0 g, 0.10 m), a crystal of iodine, and 300 ml of the stock solution were added to the magnesium turnings. The vessel was heated to 132° C to initiate the reaction. The remaining stock solution was added over a 3 hour period and the system was refluxed at 137°-144° C for a total of 123/4 hours. The crude product was decanted away from the salt. The salt cake was washed with dry toluene and the washings and crude were combined and flash distilled. A crude product, 2563 g (83.9% yield) was obtained; subsequent fractionation gave 2412 g (79% recovered yield) of 1,4-bis(n-propoxydimethylsilyl)benzene, b.p. 140°-142° C/5 mm vacuum.

Workup

  1. dry with materialMagnesium turnings (478 g, 19.7 m) in a 12 l, flask were dried
  2. customThe reactant stock solution was prepared
  3. customthe reaction
  4. additionThe remaining stock solution was added over a 3 hour period
  5. customThe crude product was decanted away from the salt
  6. washThe salt cake was washed with dry toluene
  7. distillationflash distilled
  8. customA crude product, 2563 g (83.9% yield) was obtained

Sources & evidence

ORD record
ord-75c5ba157d314f12ba7a5dede6673064
Source dataset
uspto-grants-1978_09
Patent number
US04116993

Reaction notes

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