Sodium Carbonate → Methyl 2-(4-fluorophenyl)-4-methylbenzoate

HRID 1251864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251864
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.[Cl-].[Li+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[CH:29][CH:28]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 433294Lithium ChlorideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

Produkt 1

HCID 18474522Methyl 2-(4-fluorophenyl)-4-methylbenzoateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine) palladium (9 g; 7.8 mmol) and ethanol (780 ml) was added to a suspension of methyl 4-methyl-2-trifluoromethanesulphonyloxybenzoate (58 g; 0.195 mol), 2M aqueous solution of sodium carbonate (250 ml; 0.5 mol), 4-fluorophenylboronic acid (30 g ; 0.214 mol) and lithium chloride (16.5 g ; 0.39 mol) in toluene (1.65 ml), under an argon atmosphere, The mixture was refluxed for 4 hours, diluted with ethyl acetate (1 l) and washed with aqueous sodium hydroxide solution 1N (1 l). The organic phase was evaporated and the residue purified by flash column chromatography using ethyl acetatelpetroleum ether (95:5) to give methyl 2-(4-fluorophenyl)-4-methylbenzoate (46.8 g; 99%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 4 hours
  2. washwashed with aqueous sodium hydroxide solution 1N (1 l)
  3. customThe organic phase was evaporated
  4. customthe residue purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4f4e310c66f74ef989de0ec00154098b
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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