Water → 3-(Methylthio)-4-nitrophenol

HRID 1864666노트

반응식

HRID 1864666 반응식
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][S-:13].[Na+].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:12][S:13][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 4378561Sodium methanethiolate

생성물 1

HCID 441857023-(Methylthio)-4-nitrophenol수율 90.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-fluoro-4-nitrophenol (2 g, 12.7 mmol) in dry DMF (67 mL) was added, by aliquots, 2 equivalents of sodium thiomethoxide (1.78 g, 25.5 mmol) followed by 3 equivalents of potassium carbonate (5.27 g, 38.2 mmol). The mixture was stirred at room temperature for 23 hours and then water (100 mL) was added. The mixture was extracted with EtOAc, and the combined organic layers washed successively with water (60 mL) and brine (60 mL) and then dried over MgSO4. The solvent was evaporated under vacuum to provide the title compound (2.12 g, 90%) as a yellow powder. 1H-NMR (δ, ppm, DMSO-d6): 2.44 (s, 3H, HMe), 6.72 (d, 1H, Harom 6, J6-5=9.0 Hz), 6.79 (s, 1H, Harom 2), 8.19 (d, 1H, Harom 5, J5-8=9.1 Hz), 11.20 (broad s, 1H, OH).

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic layers washed successively with water (60 mL) and brine (60 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-b5a76c8177b54b0ca67cddc23d3b0a89
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625922B2

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