Hydrogen Peroxide → 1,3-Difluoro-2-methoxy-4-nitrobenzene

HRID 243236노트

반응식

HRID 243236 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].OO.[F:16][C:17]1[C:22]([O:23][CH3:24])=[C:21]([F:25])[CH:20]=[CH:19][C:18]=1[NH2:26].[Cl-].[Na+].[OH2:29]>C(Cl)Cl>[F:25][C:21]1[CH:20]=[CH:19][C:18]([N+:26]([O-:4])=[O:29])=[C:17]([F:16])[C:22]=1[O:23][CH3:24]

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 38651622,4-Difluoro-3-methoxyanilineHCID 57417360Sodium chloride; water

생성물 1

HCID 681577701,3-Difluoro-2-methoxy-4-nitrobenzene수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of trifluoroacetic anhydride (26.2 mL, 0.19 mol) in DCM (100 mL) at 0° C. was added, dropwise, hydrogen peroxide (50% in water, 12.9 mL, 0.17 mol) and the reaction mixture was stirred at 0° C. for 1.5 h. 2,4-Difluoro-3-methoxyphenylamine (3 g, 18.9 mmol) was added as a solution in DCM (20 mL) and the reaction mixture stirred at RT for 3 h. The reaction mixture was diluted with brine and extracted with DCM (3×30 mL). The combined organic fractions were washed with sat. aq. NaHCO3 solution, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% Et2O in cyclohexane) to give the title compound as a colourless solid (2.03 g, 57%). 1H NMR 400 MHz δ (CDCl3): 7.83-7.76 (1H, m), 7.03 (1H, td, J=9.4, 2.5 Hz), 4.08 (3H, t, J=1.1 Hz).

후처리

  1. extractionextracted with DCM (3×30 mL)
  2. washThe combined organic fractions were washed with sat. aq. NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% Et2O in cyclohexane)

출처 및 근거

ORD 기록
ord-c99f3b63bec646a9971dad90cb26ee8c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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