Sulfuric Acid → 4-Bromo-1H-indene

HRID 923727Notes

Reaction equation

HRID 923727 reaction equation
[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

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 133302084-Bromo-1-indanol

Product 1

HCID 156376244-Bromo-1H-indeneYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7371366b6cdc45b1a106c376406acbfa
Source dataset
uspto-grants-2016_03
Patent number
US09279024B2

Reaction notes

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