Sodium Carbonate → Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetate

HRID 1771600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771600
[NH2:1][C:2]1[C:3]([F:10])=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 121593Isopropyl bromoacetateHCID 227559833-Amino-2,4-difluorophenol

Produkt 1

HCID 89444213Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-amino-2,4-difluoro-phenol (intermediate X(a)) (713 mg, 4.91 mmol, 1.0 eq) in DMF (20 mL) was added Na2CO3 (1.56 g, 14.8 mmol, 3.0 eq). The resulting mixture was stirred at room temperature for 35 min, then isopropyl bromoacetate (1.07 g, 5.90 mmol, 1.2 eq) was added and the reaction stirred at room temperature overnight. The reaction was diluted with water then extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:6) to give the title compound (intermediate IV(b)) as an oil (850 mg, 71%).

Aufarbeitung

  1. stirringthe reaction stirred at room temperature overnight
  2. extractionthen extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:6)

Quellen und Nachweise

ORD-Eintrag
ord-21d85328e4794c0fb05cd977bbea6f2f
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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