p-Toluenesulfonic acid → 7-Bromo-1H-indene

HRID 1646597Notes

Reaction equation

HRID 1646597 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.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(C1C=C(O)C(=CC=1)O)(C)(C)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]=[CH:6]2

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 133302084-Bromo-1-indanol

Product 1

HCID 133302097-Bromo-1H-indeneYield 89.6%

Reagents, catalysts & solvents 2

HCID 73814-tert-ButylcatecholCatalystHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

30 g of 4-bromo-1-indanol is dissolved in 720 ml of toluene, 27 g of paratoluene sulphonic acid is added, then 0.93 g of 4-tertbutylcatechol is added. The mixture is taken to reflux for one hour. After cooling to 20° C., the organic phase is washed with 25 ml of N sodium hydroxide, dried and concentrated to dryness, and the residue is chromatographed on silica, eluting with a hexane-difluoro dichloro ethane mixture (95-5), and 24.6 g of expected product is isolated.

Workup

  1. temperatureto reflux for one hour
  2. washthe organic phase is washed with 25 ml of N sodium hydroxide
  3. customdried
  4. concentrationconcentrated to dryness
  5. customthe residue is chromatographed on silica
  6. washeluting with a hexane-difluoro dichloro ethane mixture (95-5)

Sources & evidence

ORD record
ord-23675728257643ccbb8497bfff0972d3
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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