Acetic Acid → 2-(2-Fluorophenyl)oxirane

HRID 1873806Notes

Reaction equation

HRID 1873806 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH2:5].C(O)(=[O:12])C.BrN1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[CH2:5][O:12]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 123056o-Fluorostyrene

Product 1

HCID 145792542-(2-Fluorophenyl)oxiraneYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of o-fluorostyrene (5.0 g, 41.0 mmol) and acetic acid (2.33 mL, 40.9 mmol) in dioxane (33 ml) and H2O (78 ml) at 0° C. was added N-bromosuccinimide (8.02 g, 45.0 mol) in three portions. The reaction was allowed to warm to R.T and stirred overnight. Sodium carbonate (8.68 g, 81.9 mmol) was added in portions and then 1M NaOH (ca. 10 ml) was added and the reaction was stirred at RT overnight. The reaction mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 5.31 g (94%) of the title compound as a slightly tinted oil which was used without further purification. MS (ESI+) for C8H7FO m/z 138.1 (M+H)+.

Workup

  1. temperatureto warm to R.T
  2. stirringthe reaction was stirred at RT overnight
  3. customThe reaction mixture was partitioned between water and EtOAc
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic phases washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd22e8c336d7479888dfa4e8e98c6717
Source dataset
uspto-grants-2012_11
Patent number
US08304441B2

Reaction notes

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