Toluene → (2S)-2-bromo-3-phenylpropanoic acid

HRID 342269

Reaktionsgleichung

Reaktionsgleichung von HRID 342269
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.[Br-:13].[K+].N([O-])=O.[Na+].C1(C)C=CC=CC=1>S(=O)(=O)(O)O.C(O)(=O)C>[Br:13][C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([OH:12])=[O:11]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6140L-PhenylalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

Produkt 1

HCID 9816009(2S)-2-bromo-3-phenylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of L-phenylalanine (30.0 g., 0.175 mole) and potassium bromide (73.5 g., 0.618 mole) in 2.5N sulfuric acid (365 ml.) was cooled down to 0° (ice-salt bath) and treated portionwise with sodium nitrite (19.3 g., 0.28 mole) over a period of 1.0 hour. Stirring was continued for 1.0 hour at 0° and at room temperature for 1.0 hour after which the reaction mixture was extracted with ether (3×250 ml.). The combined organic extracts were washed with water (100 ml.) and brine (50 ml.), dried (anhydrous magnesium sulfate), filtered, evaporated to dryness and dried in vacuo to give 34.46 g., of product; Rf =0.45 (toluene:acetic acid, 95:5).

Aufarbeitung

  1. extractionafter which the reaction mixture was extracted with ether (3×250 ml.)
  2. washThe combined organic extracts were washed with water (100 ml.) and brine (50 ml.)
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customdried in vacuo
  7. customto give 34.46 g

Quellen und Nachweise

ORD-Eintrag
ord-ffdf2bed5c73400cb6e8aa9a844b4372
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856476

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