Ethylene Glycol → 2-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

HRID 513696ノート

反応式

HRID 513696 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]2[O:13][CH2:12][CH2:11][O:8]2)[CH:9]=1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 7363275-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolane収率 77.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a 3 neck round bottom flask, fitted with a Dean-Stark apparatus, was added 5-bromo-2-fluorobenzaldehyde (5 g, 24.6 mmol), ethane-1,2-diol (4.12 ml, 73.9 mmol), and p-toluenesulfonic acid (424 mg, 2.46 mmol). The resulting mixture was placed under nitrogen, dissolved in anhydrous toluene (100 ml) and heated under reflux for 18 h. After cooling, the mixture was concentrated in vacuo. The residue was diluted with EtOAc (50 ml) and the organic phase was washed with sat. NaHCO3 solution (30 ml), brine (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (95:5) as the eluent to give the title compound (4.69 g, 77%). The structure was confirmed by 1H NMR.

後処理

  1. customTo a 3 neck round bottom flask, fitted with a Dean-Stark apparatus
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated in vacuo
  6. additionThe residue was diluted with EtOAc (50 ml)
  7. washthe organic phase was washed with sat. NaHCO3 solution (30 ml), brine (30 ml)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by column chromatography with heptane/EtOAc (95:5) as the eluent

出典と根拠

ORDレコード
ord-c6c4602c56e7453eb347e2f3f6ab14c7
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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