Hydrogen Bromide → (2S)-2-bromo-3-phenylpropanoic acid

HRID 2255051

Reaktionsgleichung

Reaktionsgleichung von HRID 2255051
N[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BrH:13].S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[C:4]1([CH2:3][C@H:2]([Br:13])[C:10]([OH:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

Produkt 1

HCID 9816009(2S)-2-bromo-3-phenylpropanoic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Slurry L-phenylalanine (23.6 g, 143 mmol), 49% hydrobromic acid (500 g), water (500 mL) and concentrated sulfuric acid (50 mL) and cool to -5° C. Add, by dropwise addition, a solution of sodium nitrite (9.87 g, 143 mmol) in water (70 mL) over a period of about 1 hour. Stir at -5° C. to 0° C. overnight extract into ethyl ether (3×250 mL), combine the organic phases and wash with water (1×) and brine (2×). Dry (MgSO4) and evaporate the solvent in vacuo to give 3-phenyl-2(S)-bromopropionic acid as a yellow oil (26 g, 80%).

Aufarbeitung

  1. additionAdd, by dropwise addition
  2. extractionextract into ethyl ether (3×250 mL)
  3. washwash with water (1×) and brine (2×)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b1c4393983f457bbe6a0bd07ba07dbc
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05238932

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