Dichloromethane → 6-(trifluoromethyl)-1H-indene

HRID 1191930Notes

Reaction equation

HRID 1191930 reaction equation
C(Cl)Cl.[CH2:4]([C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[CH:17]=[CH2:18])C=C>C=CC1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl.CCCCC>[F:16][C:13]([F:14])([F:15])[C:11]1[CH:12]=[C:7]2[C:8]([CH:17]=[CH:18][CH2:4]2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 592126382-Allyl-4-(trifluoromethyl)-1-vinylbenzene

Product 1

HCID 190955106-(trifluoromethyl)-1H-indene

Reagents, catalysts & solvents 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichlorideCatalystHCID 8003PentaneSolvent

Procedure

Methylene chloride (0.6 L) was added to a 1 L flask containing 2-allyl-4-(trifluoromethyl)-1-vinylbenzene (80.0 g, 0.377 mol). Bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Grubbs catalyst, 1st generation) (3.1 g, 0.0038 mol) was added to the solution and the resulting solution was refluxed overnight (18 h). The solvent was evaporated to give a dark oil, which was passed through a silica gel plug using pentane. After pentane was carefully removed, 57 g (82.8%) of pure product was collected as slight brown oil. 1H NMR (400 MHz, CDCl3) δ (ppm) 7.72 (s, 1H), 7.55 (d, 1H), 7.48 (d, 1H), 6.93 (m, 1H), 6.74 (m, 1H), 3.46 (brs, 1H).

Workup

  1. temperaturethe resulting solution was refluxed overnight (18 h)
  2. customThe solvent was evaporated
  3. customto give a dark oil, which
  4. customAfter pentane was carefully removed
  5. custom57 g (82.8%) of pure product was collected as slight brown oil

Sources & evidence

ORD record
ord-7c4b1b6096ad45a79513dd564958a1fa
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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