p-Toluenesulfonic acid monohydrate → 5-bromo-1H-indene

HRID 1191935Notes

Reaction equation

HRID 1191935 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7](O)[CH2:6][CH2:5]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 27475715-bromo-1H-indeneYield 87.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-bromoindan-1-ol (5.00 g, 23.5 mmol) and p-Toluenesulfonic acid monohydrate (100 mg, 0.5 mmol) in benzene (150.00 mL) was heated to reflux for 2 h and water was continuously removed from the reaction mixture with a Dean-Stark trap. After cooling to room temperature, the benzene solution was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification of the residue by flash chromatography (hexane) yielded pure 5-bromoindene (4.0 g, 87%).

Workup

  1. temperatureto reflux for 2 h
  2. customwater was continuously removed from the reaction mixture with a Dean-Stark trap
  3. washthe benzene solution was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by flash chromatography (hexane)

Sources & evidence

ORD record
ord-016fa8e96cda43839fbca4565daf0e47
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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