HCID 15781018, compound → HCID 178425999, compound

HRID 1188267Notes

Reaction equation

HRID 1188267 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=2[OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([Li])[CH2:16][CH2:17][CH3:18].Cl[Ti:21]([Cl:33])(Cl)[C:22]1([CH3:31])[C:26]([CH3:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]1[CH3:30]>C(OCC)C>[CH3:15][C:16]1[C:6]([Ti:21]([Cl:33])([C:22]2([CH3:31])[C:23]([CH3:30])=[C:24]([CH3:29])[C:25]([CH3:28])=[C:26]2[CH3:27])[O:14][C:8]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH3:5])[C:1]([CH3:7])=[C:2]([CH3:3])[C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 15781018HCID 15781018, compoundHCID 178418339ButyllithiumHCID 178425993HCID 178425993, compound

Product 1

HCID 178425999HCID 178425999, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.90 g (10.09 mmol) of 2-phenyl-4-fluorophenol was dissolved in 80 ml of diethylether, and 4.8 ml of butyl lithium (2.5 M hexane solution) was slowly added dropwise thereto at 0° C. The mixture was allowed to react at room temperature for 5 hours, and then a solution of trichloro(pentamethylcyclopentadienyl)titanium (IV) (1.64 g, 5.5 mmol) in 10 ml of diethyl ether was slowly added dropwise thereto at −78° C. The reaction product was stirred at room temperature for 12 hours and filtered, and then volatile materials were removed therefrom. The residue was recrystallized from a mixed solvent of toluene/hexane at −35° C., thus obtaining 2.54 g of a orange-colored solid.

Workup

  1. customat 0° C
  2. customto react at room temperature for 5 hours
  3. customat −78° C
  4. filtrationfiltered
  5. customvolatile materials were removed
  6. customThe residue was recrystallized from a mixed solvent of toluene/hexane at −35° C.

Sources & evidence

ORD record
ord-fb062211e14041e0b2aef22b436f2581
Source dataset
uspto-grants-2014_03
Patent number
US08674026B2

Reaction notes

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