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

HRID 2244912Notes

Reaction equation

HRID 2244912 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-f3c535abc66649ae86f8db1a5763b1c0
Source dataset
uspto-grants-2010_03
Patent number
US07678798B2

Reaction notes

Loading…