Acetic Acid → 2-(3-Chlorophenyl)oxirane

HRID 562953

Reaction equation

HRID 562953 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH2:6].C(O)(=[O:12])C.BrN1C(=O)CCC1=O.[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[CH2:6][O:12]2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 14905m-ChlorostyreneHCID 67184N-bromobutanimide

Product 1

HCID 1556132-(3-Chlorophenyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of m-chlorostyrene (5.70 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 mmol) in three portions. The reaction was allowed to warm to R.T. After 4 hours, 2N NaOH (60 ml) was added and the reaction was allowed to stir at RT overnight. The reaction mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 6.20 g of a slightly tinted oil which was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give 6.20 g of a slightly tinted oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-eac1965d94ab478db9de2c51d14d44dd
Source dataset
uspto-grants-2011_11
Patent number
US08067450B2

Linked notes

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