N-bromobutanimide → Ethyl 2-(4-amino-3-bromophenyl)acetate

HRID 1773973

Reaktionsgleichung

Reaktionsgleichung von HRID 1773973
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O>CC#N>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[C:7]([Br:14])[CH:6]=1)[CH3:13]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 225219p-Aminophenylacetic acid ethyl ester

Produkt 1

HCID 19702145Ethyl 2-(4-amino-3-bromophenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-aminophenylacetate (1.79 g, 10 mmol, 1 eq.) in MeCN (50 mL), N-bromsuccinimide (1.78 g, 10 mmol, 1 eq.) was added slowly. The mixture was stirred at r.t. for 72 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between water (50 mL) and Et2O (50 mL). The org. phase was washed with sat. aq. NaCl soln. (1×50 mL), dried over MgSO4, and concentrated in vacuo to give (4-amino-3-bromo-phenyl)-acetic acid ethyl ester as an orange oil. The product was used without further purification.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between water (50 mL) and Et2O (50 mL)
  3. washphase was washed with sat. aq. NaCl soln
  4. dry with material(1×50 mL), dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e986737d4dab4274bb71e2f7d4a0cac2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255090B2

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