Dimethyl Sulfoxide → Methyl 4-bromo-2,6-diMethylbenzoate

HRID 2220624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220624
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([Br:14])=[CH:9][C:8]=1[CH3:15])(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CS(C)=O.[C:58]([O:61][CH2:62]C)(=[O:60])C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:14][C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([C:58]([O:61][CH3:62])=[O:60])=[C:8]([CH3:15])[CH:9]=1

Komponenten

9

Edukt 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 231343334-Bromo-2,6-dimethylphenyl trifluoromethanesulfonate

Produkt 1

HCID 23134395Methyl 4-bromo-2,6-diMethylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 4-bromo-2,6-dimethylphenyl trifluoromethanesulfonate (1.439 g), palladium acetate (0.049 g), 1,3-bis(diphenylphosphino)propane (0.089 g) and triethylamine (1.336 mL) in methanol (10 mL)/dimethylsulfoxide (15 mL) was stirred at 75° C. overnight under an atmosphere of carbon monoxide. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to afford the title compound (0.435 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-fccf88990ea948739379ddcb70bffc2c
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417169B2

Notizen zur Reaktion

Wird geladen…