Trimethylsilyl iodide → 2,6-Dibromohydroquinone

HRID 1179462노트

반응식

HRID 1179462 반응식
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([Br:10])[C:3]=1[OH:11].C[Si](I)(C)C>CC#N>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([Br:10])[C:3]=1[OH:11]

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodide2회HCID 137237142,6-Dibromo-4-methoxyphenol

생성물 1

HCID 768522,6-Dibromohydroquinone수율 98.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Dissolve 2,6-dibromo-4-methoxyphenol (23.0 g, 80.6 mmol) in CH3CN (400 mL) and add trimethylsilyl iodide (TMSI) (53 mL, 371 mmol). Reflux the solution for 4 hours and add more TMSI (50 mL, 371 mmol). Heat the reaction at reflux overnight and cool to ambient temperature. Pour into ice-H2O (700 mL) and extract with EtOAc (2×300 mL). Wash the combined extracts with saturated sodium hydrosulfite (200 mL), H2O (200 mL) and brine (100 mL), dry over MgSO4, filter and concentrate. Crystallize the residue to provide the subtitled product (21.36 g, 98%) as a tan crystalline solid.

후처리

  1. temperatureReflux the solution for 4 hours
  2. temperatureHeat
  3. customthe reaction
  4. temperatureat reflux overnight
  5. extractionextract with EtOAc (2×300 mL)
  6. washWash the combined extracts with saturated sodium hydrosulfite (200 mL), H2O (200 mL) and brine (100 mL)
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customCrystallize the residue

출처 및 근거

ORD 기록
ord-afadf83d216d4984b1d357d01498764b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279499B2

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