2-Bromoethyl p-bromophenyl ether → 1-Bromo-4-(ethenyloxy)benzene

HRID 646149Notes

Reaction equation

HRID 646149 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10]Br)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]=[CH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 877972-Bromoethyl p-bromophenyl etherHCID 23665647Potassium tert-butoxide

Product 1

HCID 114013721-Bromo-4-(ethenyloxy)benzeneYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-4-(2-bromoethoxy)benzene (19.9 g, 100 mmol; see step (a) above) in THF (120 mL) was portion-wise added t-BuOK (14.0 g, 125 mmol) over 10 min at 0° C. After stirring at room temperature for 16 h, the mixture was diluted with water (400 mL) and the product was extracted with light petrol (4×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), concentrated and distilled under vacuum to yield the sub-title compound (11.5 g, 58%).

Workup

  1. extractionthe product was extracted with light petrol (4×100 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-524fb7489f5d431f97dd0cea24560d0c
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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