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

HRID 2387452Notes

Reaction equation

HRID 2387452 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-8da8f80d97654c048fd6dc3ac1af62b5
Source dataset
uspto-grants-2012_09
Patent number
US08268826B2

Reaction notes

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