4,6-Dibromoisochroman-1-one → 6-bromo-1H-isochromen-1-one

HRID 2173151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173151
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5](=[O:13])[O:4][CH2:3]1>C(Cl)Cl>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:13])[O:4][CH:3]=[CH:2]2

Komponenten

3

Edukt 1

HCID 675174614,6-Dibromoisochroman-1-one

Produkt 1

HCID 212520476-bromo-1H-isochromen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4,6-dibromo-3,4-dihydro-1H-isochromen-1-one (1.76 g, 5.75 mmol) was dissolved in DCM (15 mL) then added TEA (20 mL, 143 mmol) and stirred at room temperature for 72 hrs. The mixture was concentrated then took up the residue with DCM and washed with 1N HCl. Repeated the wash with brine then dried over Na2SO4 and evaporated to dryness. The residue was purified by MPLC with 0-100% ETOAc/hexane to yield 6-bromo-1H-isochromen-1-one. LC-MS (IE, m/z): 227 [M+2]+; 1H-NMR (500 MHz, CDCl3) δ ppm 8.18 (d, J=8.5 Hz, 1H), 7.67 (dd, J=1.8, 6.4 Hz, 1H), 7.64 (d, J=1.9 Hz, 1H), 7.33 (d, J=5.7 Hz, 1H), 6.47 (d, J=5.8 Hz, 1H).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. washwashed with 1N HCl
  3. washwash with brine
  4. dry with materialthen dried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by MPLC with 0-100% ETOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6a915787210e4af29242de1345cb4a6f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

Notizen zur Reaktion

Wird geladen…