1-(2-Chloroethoxy)-2-iodo-4-(trifluoromethoxy)benzene → 1-(Vinyloxy)-2-iodo-4-(trifluoromethoxy)benzene

HRID 1267885Notes

Reaction equation

HRID 1267885 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[I:16].CC(C)([O-])C.[K+]>O1CCCC1>[CH:3]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][C:6]=1[I:16])=[CH2:2]

Participants

4

Reactant 2

HCID 109046421-(2-Chloroethoxy)-2-iodo-4-(trifluoromethoxy)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 110020251-(Vinyloxy)-2-iodo-4-(trifluoromethoxy)benzeneYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(2-chloroethoxy)-2-iodo-4-(trifluoromethoxy)benzene (Description 10; 12.1 g, 33 mmol) in tetrahydrofuran (50 mL) at −5° C. was slowly added potassium tert-butoxide (3.7 g, 33 mmol). After addition was complete, the solution was allowed to stir to room temperature for 20 hours, and was then quenched with water (100 mL). The mixture was extracted with 50% diethyl ether/hexane (2×100 mL) and the extracts dried (MgSO4). Concentration gave an oil which was purified by silica chromatography to give the title compound as an oil (7.62 g, 23 mmol).

Workup

  1. customat −5° C.
  2. additionAfter addition
  3. customwas then quenched with water (100 mL)
  4. extractionThe mixture was extracted with 50% diethyl ether/hexane (2×100 mL)
  5. dry with materialthe extracts dried (MgSO4)
  6. concentrationConcentration
  7. customgave an oil which
  8. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-171dee239f3f4c419214631580bdf566
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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