Water → 7-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran

HRID 726612

Reaktionsgleichung

Reaktionsgleichung von HRID 726612
[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([Br:13])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine

Produkt 1

HCID 537220087-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuranAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A stirred solution of 10.0 grams (0.061 mole) of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran in 150 mL of N,N-dimethylformamide is cooled in an ice-water bath, and a solution of 10.9 grams (0.061 mole) of N-bromosuccinimide in 50 mL of N,N-dimethylformamide is added in one portion. Upon completion of addition, the reaction mixture is maintained in the ice-water bath for about one hour After this time the reaction mixture is poured into about 600 mL of water. The mixture is then extracted with two 200 mL portions of diethyl ether. The combined extracts are washed with two 100 mL portions of an aqueous 10% lithium chloride solution. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 12.3 grams of 7-amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum is consistent with the proposed structure.

Aufarbeitung

  1. additionUpon completion of addition
  2. extractionThe mixture is then extracted with two 200 mL portions of diethyl ether
  3. washThe combined extracts are washed with two 100 mL portions of an aqueous 10% lithium chloride solution
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d0096e64811a4ecd96ee148cc5e54fe5
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05710157

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