Hydrochloric Acid → 4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propyl-3'-vinylbiphenyl

HRID 1690163Notes

Reaction equation

HRID 1690163 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:22][CH2:23][O:24][CH3:25])([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[CH2:26][CH2:27][CH3:28])(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:39]([C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1)=[CH2:40].Cl>O1CCOCC1.O>[F:16][C:14]([F:17])([F:15])[C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:45]2[CH:44]=[CH:43][CH:42]=[C:41]([CH:39]=[CH2:40])[CH:46]=2)=[C:8]([CH2:26][CH2:27][CH3:28])[CH:9]=1)([O:22][CH2:23][O:24][CH3:25])[C:18]([F:20])([F:19])[F:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 43668863-Vinylphenylboronic Acid (contains varying amounts of Anhydride)HCID 592010014-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenyl trifluoromethanesulfonate

Product 1

HCID 592010644-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propyl-3'-vinylbiphenylYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenyl trifluoromethanesulfonate (238 mg, 497 μmol) in 1,4-dioxan, potassium phosphate (401 mg), 3-vinylphenylboronic acid (88 mg), and tetrakis triphenylphosphine palladium complex (57 mg) were added at room temperature under an argon atmosphere, and the resultant mixture was heated at 80° C. After completion of the reaction, the reaction solution was neutralized by adding water and 2 mol/L of hydrochloric acid, extracted with ethyl aceate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and the title compound (175 mg, yield 81%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl aceate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-b9accc3b25b341fa90973360fe179148
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

Loading…