Bromine → 7-Amino-8-bromo-3,4-dihydronaphthalen-1(2H)-one

HRID 361391

Reaktionsgleichung

Reaktionsgleichung von HRID 361391
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:13]Br>C(O)(=O)C>[NH2:1][C:2]1[C:11]([Br:13])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24408Bromine2×HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 154628587-Amino-8-bromo-3,4-dihydronaphthalen-1(2H)-oneAusbeute 102,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

7-Amino-1-tetralone (457 mg, 2.83 mmol) was dissolved in acetic acid (8 mL) and treated with bromine (150 mL, 2.91 mmol) dropwise. After 10 min., more bromine (17 mL) was added. Then the solvent was evaporated off to give a light brown solid. It was partitioned between Na2CO3 solution and EtOAc From the organic phase was obtained a semi-solid (696 mg). It was dissolved in CHCl3 and flash chromatographed over silica gel 50 g) eluting with EtOAc/hexane (1:4) to afford a yellow solid (320 mg, 470 yield): mp 93°-96° C.

Aufarbeitung

  1. customThen the solvent was evaporated off
  2. customto give a light brown solid
  3. customIt was partitioned between Na2CO3 solution and EtOAc From the organic phase

Quellen und Nachweise

ORD-Eintrag
ord-6f472eee9bd542b1a9772e6913725100
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866579

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