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

HRID 513696노트

반응식

HRID 513696 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c6c4602c56e7453eb347e2f3f6ab14c7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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