p-Toluenesulfonic acid monohydrate → 5,7-Difluoro-2-methyl-1H-indene

HRID 574639Notes

Reaction equation

HRID 574639 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[CH:6]2O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:11][C:9]1[CH:8]=[C:7]2[C:3](=[C:2]([F:1])[CH:10]=1)[CH2:4][C:5]([CH3:13])=[CH:6]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 797261264,6-Difluoro-2-methyl-indan-1-ol

Product 1

HCID 894467565,7-Difluoro-2-methyl-1H-indeneYield 85.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to Scheme 3, step 3: A mixture of 4,6-Difluoro-2-methyl-indan-1-ol (8a) (0.65 g, 3.53 mmol) and para-toluene sulfonic acid monohydrate (30 mg, 0.18 mmol) in toluene was heated at reflux for 1 h. The solution was washed with aqueous saturated NaHCO3 and brine, dried over MgSO4 and solvents evaporated. The crude product was purified by silica gel chromatography (eluting with 0% to 100% ethyl acetate in heptane to give 0.50 g of 5,7-Difluoro-2-methyl-1H-indene (9a) which was used immediately in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. washThe solution was washed with aqueous saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4 and solvents
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography (
  7. washeluting with 0% to 100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-82288b6ee84d4a09a4c094c495c7b173
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

Loading…