Sulfuric Acid → 4-Bromo-1H-indene

HRID 923727ノート

反応式

HRID 923727 の反応式
[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

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 133302084-Bromo-1-indanol

生成物 1

HCID 156376244-Bromo-1H-indene収率 69.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7371366b6cdc45b1a106c376406acbfa
出典データセット
uspto-grants-2016_03
特許番号
US09279024B2

反応ノート

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