p-Toluenesulfonic acid monohydrate → 7-bromo-5-fluoro-1H-indene
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureat reflux for 2.5 h
- washThe solution was washed with aqueous saturated NaHCO3 and brine
- dry with materialdried over MgSO4 and solvents
- customevaporated
Sources & evidence
- ORD record
- ord-b4dcc7b80f3d418a813895f273aa228f
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034897B2
Reaction notes
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