Ethyl bromoacetate → Ethyl 2-(3-amino-2,4-difluorophenoxy)acetate

HRID 1771593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771593
[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][CH2:22][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][CH2:22][CH3:23])=[O:20]

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 227559833-Amino-2,4-difluorophenol

Produkt 1

HCID 89437136Ethyl 2-(3-amino-2,4-difluorophenoxy)acetateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-amino-2,4-difluorophenol (intermediate X(a)) (713 mg, 4.9 mmol, 1.0 eq) in DMF (30 mL) was added Na2CO3 (1.56 g, 14.7 mmol, 3.0 eq). The resulting mixture was stirred for 40 min at room temperature. Ethyl bromoacetate (1 g, 5.90 mmol 1.2 eq) was added and the reaction stirred 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 (petroleum ether: EtOAc, 25:1) to give the title compound (intermediate IV(a)) as an oil (850 mg, 71%).

Aufarbeitung

  1. stirringthe reaction stirred 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 (petroleum ether: EtOAc, 25:1)

Quellen und Nachweise

ORD-Eintrag
ord-1f5717139262433da3f417cdb136f1bc
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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