Sodium Carbonate → 2-Chloro-4-(5-chloro-2-methoxyphenyl)benzoic acid

HRID 1695136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695136
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:22][CH3:23])=[C:17]([CH:21]=1)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[Cl:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[C:13]([Cl:12])[CH:21]=[CH:17][C:16]=2[O:22][CH3:23])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 769705-Chloro-o-anisic acidHCID 1088294-Bromo-2-chlorobenzoic acid

Produkt 1

HCID 532275772-Chloro-4-(5-chloro-2-methoxyphenyl)benzoic acidAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-bromo-2-chlorobenzoic acid (0.4 g), 5-chloro-2-methoxybenzoic acid (0.4 g), Pd(dppf)Cl2 (0.12 g), sodium carbonate (0.9 g), dioxan (15 ml) and methanol (5 ml) were charged to a flask and heated at reflux for 16 h. Cooled to room temp and filtered (hyflo). The filtrate was concentrated in vacuo, then dissolved in ethyl acetate. The suspension was made basic by addition of dilute NaOH. The aqueous layer was separated and acidified using 2M HCl, extracted with EtOAc, dried (MgSO4) and evaporated in vacuo to give the sub-title compound Yield 0.4 g

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered (hyflo)
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in ethyl acetate
  6. additionThe suspension was made basic by addition of dilute NaOH
  7. customThe aqueous layer was separated
  8. extractionextracted with EtOAc
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3bddcae30454e089b5fd4a6d06f4e49
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163727B2

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