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Boron tribromide → 7-Amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one

HRID 1037371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1037371
[NH2:1][C:2]1[C:11]([O:12]C)=[C:10]2[C:5]([C:6](=[O:21])[C:7]([I:20])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([I:20])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:9]2)=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 670677907-Amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one

Produkt 1

HCID 670679197-Amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-oneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 7-amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one (494 mg, 1.26 mmol) in DCM (25 mL) under a nitrogen atmosphere at −78° C. was added a solution of BBr3 (1 M in DCM, 8 mL, 8 mmol) dropwise over 15 mins. The mixture was stirred at −78° C. for 1 hour before allowing to warm to RT and stirred for a further 18 hours. The reaction mixture was quenched with the slow addition of saturated aqueous NaHCO3. DCM was added and the resulting biphasic mixture was separated. The aqueous layer was extracted with DCM (2×50 mL) and the combined organic phase was washed with brine, dried (NaSO4), filtered, and the solvent removed to give the title compound as a brown solid (405 mg, 85%). LCMS (Method G): RT=3.04 min, [M+H]+=380.

Aufarbeitung

  1. temperatureto warm to RT
  2. stirringstirred for a further 18 hours
  3. customThe reaction mixture was quenched with the slow addition of saturated aqueous NaHCO3
  4. additionDCM was added
  5. customthe resulting biphasic mixture was separated
  6. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  7. washthe combined organic phase was washed with brine
  8. dry with materialdried (NaSO4)
  9. filtrationfiltered
  10. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-7193569dd6974b5caff581f3a341131f
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546376B2

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