Trimethylsilyl iodide → 2,6-Dibromohydroquinone

HRID 1179462ノート

反応式

HRID 1179462 の反応式
[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]

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodide2 回HCID 137237142,6-Dibromo-4-methoxyphenol

生成物 1

HCID 768522,6-Dibromohydroquinone収率 98.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-afadf83d216d4984b1d357d01498764b
出典データセット
uspto-grants-2007_10
特許番号
US07279499B2

反応ノート

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