Diethyl Sulfate → 3-Chloro-4-fluorophenetole

HRID 2095624ノート

反応式

HRID 2095624 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:10](OS(OCC)(=O)=O)[CH3:11].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

5

反応物 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 757903-Chloro-4-fluorophenol

生成物 1

HCID 27737033-Chloro-4-fluorophenetole

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 3-chloro-4-fluorophenol (2.0 g, 13.7 mmol), diethylsulfate (1.58 mL, 17.8 mmol) and K2CO3 (9.4 g, 68.5 mmol) in acetone (20 mL) was heated under refluxed for 3 h. The reaction mixture was filtered and concentrated. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine. The organic layer was dried (Na2SO4) and concentrated to give the title compound as a liquid. 1H NMR (CDCl3, 400 MHz): δ=1.39 (t, 3H, J=7.2 Hz), 3.97 (q, 2H, J=7.2 Hz), 6.71-6.74 (m, 1H), 6.89-6.91 (m, 1H), 7.02 (t, 1H, J=8.8 Hz).

後処理

  1. temperaturewas heated
  2. temperatureunder refluxed for 3 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. additionThe residue was diluted with ethyl acetate (50 mL)
  6. washwashed with water (30 mL) and brine
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1d69fe330c7c483785a8c4dc4a4b67f5
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

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