Sodium Thiosulfate → 4-Bromo-2-fluoro-3,5-dimethylphenol

HRID 15642

反応式

HRID 15642 の反応式
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[O-]S(C(F)(F)[F:16])(=O)=O.F[N+]1C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([F:16])[C:3]=1[CH3:10]

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 819704-Bromo-3,5-dimethylphenolHCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)

生成物 1

HCID 593425984-Bromo-2-fluoro-3,5-dimethylphenol収率 36.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 4-bromo-3,5-dimethylphenol (2.00 g, 9.95 mmol) in 1,2-dichloroethane (20 mL) was added N-fluoropyridinium triflate (6.15 g, 24.9 mmol), and the mixture was heated under reflux for 7 hr. The reaction mixture was treated with 1 M aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.790 g, yield 36%) as a colorless oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

出典と根拠

ORDレコード
ord-cbdc6c6d5028454a97a4fb8644a9ff86
出典データセット
uspto-grants-2010_06
特許番号
US07732626B2

関連ノート

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