Acetic Acid → 2-(3-Fluorophenyl)oxirane

HRID 562939

반응식

HRID 562939 반응식
[F: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>[F:1][C:2]1[CH:3]=[C:4]([CH:5]2[CH2:6][O:12]2)[CH:7]=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 676913-Fluorostyrene

생성물 1

HCID 152939162-(3-Fluorophenyl)oxirane수율 111.5%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of m-fluorostyrene (5.00 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 RT. After 4 hours, 2N NaOH (60 ml) was added and the reaction was left 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 6.30 g of the title compound as a slightly tinted oil which was used without further purification.

후처리

  1. waitthe reaction was left
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-401201bccdab428d8118c9da64818ac2
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067450B2

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