m-Chloroperbenzoic acid → 4-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

HRID 1848524노트

반응식

HRID 1848524 반응식
[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:13].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[F:1][C:2]1[C:10]([CH:11]2[CH2:12][O:22]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:13]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 666441764-fluoro-5-vinyl-3H-isobenzofuran-1-one

생성물 1

HCID 595686724-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-fluoro-5-vinyl-3H-isobenzofuran-1-one (4.0 g, 17.3 mmol) in 100 mL of DCM was slowly added mCPBA (6.0 g, 85% purity, 34.6 mmol) in 50 mL of DCM at 0° C. After warming to room temperature, the mixture was stirred overnight. The mixture was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers were washed with brine and then concentrated. The residue was purified by column chromatography to give 4-fluoro-5-oxiranyl-3H-isobenzofuran-1-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=7.8 Hz, 1H), 7.37-7.40 (m, 1H), 5.37 (s, 2H), 4.21-4.22 (m, 1H), 3.25-3.27 (m, 1H), 2.80-2.82 (m, 1H).

후처리

  1. customat 0° C
  2. washThe mixture was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washThe organic layers were washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a4b1c3eac94449b8a316ceacdc9ec213
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952166B2

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