p-Toluenesulfonic acid monohydrate → HCID 68462193, compound

HRID 574634Notes

Reaction equation

HRID 574634 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]=[CH:6]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 894444374-Bromo-6-fluoro-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 68462193HCID 68462193, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to Scheme 2, step 2: A mixture of 4-bromo-6-fluoro-indan-1-ol (4a) (10.0 g, 43.3 mmol) and para-toluene sulfonic acid monohydrate (372 mg, 2.16 mmol) in toluene was heated at reflux for 2.5 h. The solution was washed with aqueous saturated NaHCO3 and brine, dried over MgSO4 and solvents evaporated to give 9.0 g of 7-Bromo-5-fluoro-1H-indene (5a) which was used immediately in the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. washThe solution was washed with aqueous saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4 and solvents
  5. customevaporated

Sources & evidence

ORD record
ord-b4dcc7b80f3d418a813895f273aa228f
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

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