Acetone → O-Terphenyl

HRID 1176944

Reaction equation

HRID 1176944 reaction equation
C[Si](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12](I)=[CH:11][C:10]=2F)=[C:5](F)[C:4]=1F.C([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)CC.OCC(C)(CO)C.CC(C)=O>CC(O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:6]1([C:9]2[C:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 31344Neopentyl glycolHCID 4100861(4-Propylphenyl)boronic acidHCID 11304300Trimethyl(2,3,2'-trifluoro-4'-iodobiphenyl-4-yl)silane2×

Product 1

HCID 6766O-TerphenylYield 89%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of (2 mmol) of 8, (2.2 mmol) of 4-propylphenylboronic acid, 250 mg (2.40 mmol) of neopentyl glycol, 1.53 g (4.84 mmol) of Ba(OH)2 8 H2O, 1.35 ml (0.103 mmol, 5 mol %) of a 76 mM acetone solution of Pd(OAc)2 in 20 ml of 95% i—PrOH is stirred at 80° C. for 12 hours. The solvent is subsequently removed under reduced pressure. 5 ml of 2 M HCl are added to the residue, and the mixture is extracted with dichloromethane (3×5 ml). The combined organic phases are dried over MgSO4 and filtered through SiO2. The solvent is removed under reduced pressure, and the residue is converted into 10 (yield: 89%).

Workup

  1. customThe solvent is subsequently removed under reduced pressure
  2. addition5 ml of 2 M HCl are added to the residue
  3. extractionthe mixture is extracted with dichloromethane (3×5 ml)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered through SiO2
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-de98e425693a48bca8f2833cf7957733
Source dataset
uspto-grants-2010_11
Patent number
US07842845B2

Linked notes

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