Dichloromethane → HCID 86762481, compound

HRID 406386Notes

Reaction equation

HRID 406386 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH3:14])[CH:7]=1)(O)[CH3:4].Cl[CH2:18]Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]([CH3:18])([CH3:4])[C:2]([F:16])([F:15])[F:1])=[CH:7][C:8]=1[CH3:14]

Participants

4

Reactant 2

HCID 6344Dichloromethane2×HCID 66618813HCID 66618813, compound

Product 1

HCID 86762481HCID 86762481, compound

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Conditions

Temperature
-70 °C

Procedure

To an ice-cold solution of 1,1,1-trifluoro-2-(4-methoxy-3-methylphenyl)-propane-2-ol (440 mg) in dichloromethane (20 ml) were added titanium tetrachloride (357 mg). Under the same temperature, it was stirred for 2 hours. Ice-cold water and dichloromethane were added to the organic layer and the organic layer was separated. The obtained organic layer was washed with saturated sodium bicarbonate solution and dried over anhydrous potassium carbonate. After removing the drying agent, the organic layer was concentrated under reduced pressure. After the residue was dissolved in dichloro methane (15 ml), it was cooled at −70° C. and titanium tetrachloride (302 mg) and dimethylzinc (1M, n-hexane solution, 3.18 ml) was added. The mixture was brought back to room temperature and stirred for 3 hours. Ice-cold water and dichloromethane were added to the solution and the organic layer was separated. The obtained organic layer was washed with saturated sodium bicaronate solution and then dried over anhydroous magnesium sulfate. After removing the drying agent, the organic layer was concentrated under reduced pressure.

Workup

  1. customthe organic layer was separated
  2. washThe obtained organic layer was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous potassium carbonate
  4. customAfter removing the drying agent
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. dissolutionAfter the residue was dissolved in dichloro methane (15 ml)
  7. additiontitanium tetrachloride (302 mg) and dimethylzinc (1M, n-hexane solution, 3.18 ml) was added
  8. customwas brought back to room temperature
  9. stirringstirred for 3 hours
  10. additionIce-cold water and dichloromethane were added to the solution
  11. customthe organic layer was separated
  12. washThe obtained organic layer was washed with saturated sodium bicaronate solution
  13. dry with materialdried over anhydroous magnesium sulfate
  14. customAfter removing the drying agent
  15. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a51f6d4e2c5246cc8a157a7c2fd93f80
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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