m-Chloroperbenzoic acid → 6-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

HRID 1501987

반응식

HRID 1501987 반응식
[CH:1]([C:3]1[C:4]([CH3:12])=[C:5]([C:8]([F:11])=[CH:9][CH:10]=1)[C:6]#[N:7])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[F:11][C:8]1[C:5]([C:6]#[N:7])=[C:4]([CH3:12])[C:3]([CH:1]2[CH2:2][O:21]2)=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 666438663-Ethenyl-6-fluoro-2-methylbenzonitrile

생성물 1

HCID 866473076-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Ethenyl-6-fluoro-2-methylbenzonitrile (14.9 g, 92.0 mmol) was added to DCM (400 mL) at 0° C. then mCPBA (47.85 g, 277.5 mmol) was added and the mixture was stirred at RT for 72 h. The reaction mixture was washed with saturated aqueous Na2S2O3, then with 1N NaOH, and brine. The organic layer was separated, dried over Na2SO4, filtered, and evaporated to dryness. The crude product was purified by chromatography through a 330 g Redi-sep column, eluting with 0-100% hexane/DCM solvent system to afford 6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile. LC-MS: M+1=178.

후처리

  1. washThe reaction mixture was washed with saturated aqueous Na2S2O3
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by chromatography through a 330 g Redi-sep column
  7. washeluting with 0-100% hexane/DCM solvent system

출처 및 근거

ORD 기록
ord-ece37e959a7b494f8a59842fed09652b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206199B2

연결된 노트

불러오는 중…