Bromine → 2-Bromo-7-iodo-9H-fluoren-9-one

HRID 902989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902989
[I:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC(OC(C)=O)=O.CC(O)=O.[Br:42]Br>S(=O)(=O)(O)O.C(O)(=O)C>[Br:42][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][C:2]([I:1])=[CH:14][CH:13]=3)[C:5](=[O:15])[C:6]=2[CH:7]=1

Komponenten

7

Edukt 4

HCID 24408BromineHCID 2486172-Iodo-9-fluorenoneHCID 12217721Iodo benzene diacetateHCID 21895370AcOH AcOAc

Produkt 1

HCID 574398702-Bromo-7-iodo-9H-fluoren-9-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A suspension of 2-iodofluoren-9-one (1.046 g, 3.42 mmol; Maybridge) and iodobenzene diacetate (1.21.g, 3.76 mmol; Aldrich) in 1:1 Ac2O-HOAc (10 mL) was treated with bromine (180 μL, 3.48 mmol; Aldrich) followed by 3 drops concentrated sulfuric acid. The mixture solidified, so it was diluted with acetic acid until it could be stirred. After 2 h, the reaction was quenched with aq. Na2S2O3, neutralized with K2CO3, and filtered. The solid filter cake was washed with water, dried, and recrystallized from hot EtOH to afford the title compound (1.05 g, 2.73 mmol; 80% yield): 1H NMR (300 MHz, CDCl3) δ ppm 7.97 (dd, J=2, 1 Hz, 1H), 7.84 (dd, J=8, 2 Hz, 1H), 7.75-7.79 (m, 1H), 7.63 (dd, J=8, 2 Hz, 1H), 7.39 (d, J=7 Hz, 1H), 7.24-7.31 (m, 1H); MS (DCl/NH3): m/z 384 (M+1)+, 386 (M+3)+.

Aufarbeitung

  1. customthe reaction was quenched with aq. Na2S2O3
  2. filtrationfiltered
  3. filtrationThe solid filter cake
  4. washwas washed with water
  5. customdried
  6. customrecrystallized from hot EtOH

Quellen und Nachweise

ORD-Eintrag
ord-ab5b3a0a995643d8acf7c696ea835206
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365193B2

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