Bromine → 2,6-dibromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

HRID 1684866

Reaktionsgleichung

Reaktionsgleichung von HRID 1684866
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[Br:14]Br>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]([Br:14])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 102433122-bromo-6,7,8,9-tetrahydro-5H-benzo(7)annulen-5-one

Produkt 1

HCID 672659642,6-dibromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Example 3, 2-Bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (1.5 g, 5.9 mmol) was dissolved Et2O (25 mL), cooled to 0° C. and bromine (0.35 mL, 6.6 mmol) was added dropwise. The solution was stirred at 24° C. until TLC indicated reaction complete (2-18 h; scale dependent). The solvent was removed by rotory evaporation and the crude product applied to a 25 (M) Biotage® silica gel column. Gradient elution from 50-100% B (A=Hexanes; B=10% EtOAc/hex) over 500 mL and gave 2,6-dibromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one 700 mg, and 1.5 g of a second fraction containing dibromide (1:1). RT=2.2 minutes (condition 1).

Aufarbeitung

  1. customreaction complete (2-18 h; scale dependent)
  2. customThe solvent was removed by rotory evaporation
  3. washGradient elution from 50-100% B (A=Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c43970141c9d45e3885f0b0716f641d1
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08147818B2

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