Sulfuric Acid → 4-Bromo-1H-indene

HRID 1772395노트

반응식

HRID 1772395 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2O.S(=O)(=O)(O)O>O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 133302084-Bromo-1-indanol

생성물 1

HCID 156376244-Bromo-1H-indene수율 69.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Compound 3 (150 g, 704 mmol, 1 equiv) was suspended in a mixture of concentrated sulfuric acid (250 mL) and water (1.25 L). The mixture was refluxed overnight. The reaction was cooled and extracted with 1.5 L of dichloromethane. The organic layer was washed with saturated sodium bicarbonate (1.5 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified over silica gel (800 g), eluting with heptanes to give compound 4 (95 g, 69% yield) as a light yellow oil.

후처리

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe reaction was cooled
  3. extractionextracted with 1.5 L of dichloromethane
  4. washThe organic layer was washed with saturated sodium bicarbonate (1.5 L)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel (800 g)
  8. washeluting with heptanes

출처 및 근거

ORD 기록
ord-65f53032bd824850ae022e8038dbe5a2
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249239B2

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