Water → 1,2,4-Trifluoro-5-methanesulfinyl-benzene

HRID 2066854노트

반응식

HRID 2066854 반응식
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[C:17]([S:19][CH3:20])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[OH2:23]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])=[O:9])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])(=[O:9])=[O:23])[C:16]([F:21])=[CH:15][C:14]=1[F:22]

참가 물질

7

반응물 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 467394612,4,5-Trifluorothioanisole

생성물 2

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzene수율 14%HCID 673085031,2,4-Trifluoro-5-methanesulfinyl-benzene수율 24%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

MCPBA (4.93 g, 22 mmol) in DCM (20 mL) was added to an ice cooled solution of 43a (22 mmol) in DCM (40 mL). After 2 h, the mixture was diluted with water (30 mL) and saturated NaHCO3 (30 mL) and stirred for 20 minutes. The organic layer was removed and the aqueous layer was extracted with DCM (2×20 mL). The combined organic extracts were dried and concentrated. The residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane) to afford 1,2,4-trifluoro-5-methanesulfinyl-benzene 43b (0.41 g, 24% yield, HPLC, LC-MS 195.0 (MH)) and 1,2,4-trifluoro-5-methanesulfonyl-benzene 43c (0.63 g, 14%) as white powders.

후처리

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane)

출처 및 근거

ORD 기록
ord-7bcaf7230a314be98cb59779fd5f5fe0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293729B2

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