Ethanol → Ethyl 2-(4-amino-2-fluorophenyl)acetate

HRID 889500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889500
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[C:8]([F:16])[CH:7]=1.[CH2:17](O)[CH3:18]>>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH2:17][CH3:18])=[O:14])=[C:8]([F:16])[CH:7]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 187943492-(4-Amino-2-fluorophenyl)acetic acid

Produkt 1

HCID 15840528Ethyl 2-(4-amino-2-fluorophenyl)acetate

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Thionyl chloride (986 mL, 8.51 mol) was added dropwise to a stirred suspension of 2-(4-amino-2-fluorophenyl)acetic acid (960 g, 5.68 mol) in ethanol (10 L) at 0° C. under a nitrogen atmosphere. The reaction mixture was then heated to 40° C. for 48 hours, with the reaction progress monitored by 1H-nmr spectroscopy. The reaction mixture was evaporated to dryness and the residue redissolved in a mixture of dichloromethane (8 L) and saturated sodium hydrogen carbonate solution (5 L). Further sodium hydrogen carbonate solution was added (˜8 L) until the aqueous phase was basic. The layers were separated and the organic phase washed with saturated sodium hydrogen carbonate solution (4 L), dried over magnesium sulphate and the solvent removed under reduced pressure gave the desired product, ethyl (4-amino-2-fluorophenyl)acetate, as an orange oil (1042 g, 93% yield), that may crystallise upon standing.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue redissolved in a mixture of dichloromethane (8 L) and saturated sodium hydrogen carbonate solution (5 L)
  3. additionFurther sodium hydrogen carbonate solution was added (˜8 L) until the aqueous phase
  4. customThe layers were separated
  5. washthe organic phase washed with saturated sodium hydrogen carbonate solution (4 L)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a9636558b1e14f57895b543495d3e5cd
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252833B2

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