Water → 3-(Methylthio)-4-nitrophenol

HRID 658464ノート

反応式

HRID 658464 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 441857023-(Methylthio)-4-nitrophenol収率 91.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-fluoro-4-nitrophenol (3.0 g, 19.1 mmol) in anhydrous DMF (100 mL) was added dropwise sodium thiomethoxide (2.57 mL, 38.2 mmol, 2.0 eq) followed by potassium carbonate (7.92 g, 57.3 mmol, 3.0 eq), and the reaction mixture was stirred at RT for 18 h. Water was then added to quench the solution, and the reaction mixture was extracted with EtOAc (3×250 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, and evaporated under reduced pressure. Purification of the crude using MPLC (biotage) eluted with 20% EtOAc—hexanes afforded 3.25 g (91.9%) of 3-(methylsulfanyl)4-nitrophenol as a yellow solid.

後処理

  1. customto quench the solution
  2. extractionthe reaction mixture was extracted with EtOAc (3×250 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customPurification of the crude
  7. washeluted with 20% EtOAc—hexanes

出典と根拠

ORDレコード
ord-c0d6c3ff153a4f0882a5e81eec7bc60a
出典データセット
uspto-grants-2011_12
特許番号
US08076488B2

反応ノート

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