Hydrochloric Acid → 2-Chloro-5-methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid

HRID 2184455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184455
I[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.[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>[Cl:11][C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]([O:12][CH3:13])=[CH:3][C:2]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:15]([F:26])([F:25])[F:14]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 167918585-Chloro-4-iodo-2-methoxybenzoic acid

Produkt 1

HCID 219477542-Chloro-5-methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-iodo-5-chloro-2-methoxy benzoic acid of Step A (3.12 g, 10 mmol) in N,N-dimethylformamide (100 mL) was added 2-trifluoromethyl-phenyl boronic acid (5.70 g, 30 mmol) and potassium carbonate (12.73 g, 92 mmol). This mixture was purged with nitrogen and then treated with a catalytic amount of tetrakis(triphenylphosphine) palladium(0) (0.58 g, 0.5 mmol). The reaction was heated to reflux overnight, cooled, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to provide a nearly quantitative amount of the title acid which was used in the next step without further purification.

Aufarbeitung

  1. customThis mixture was purged with nitrogen
  2. temperatureThe reaction was heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-91e3d69560ed4a6b8d54ee968ece86f6
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900200B2

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