Boron tribromide → HCID 25149596, Verbindung

HRID 2108606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108606
[I:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([I:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.B(Br)(Br)Br>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([I:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 25149595HCID 25149595, Verbindung

Produkt 1

HCID 25149596HCID 25149596, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenol (0.28 g, 0.55 mmol) in dichloromethane (17.0 mL) at −78° C. was added BBr3 (13.1 mL, 13.1 mmol, 1.0 M solution in CH2Cl2). The reaction mixture was stirred at −78° C. for 10 min, allowed to warm to room temperature and stirred for 16 h. The reaction mixture was poured into ice and extracted with CH2Cl2 (20 mL×2). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with acetone-hexanes (3:7) to afford 3,5-diiodo-4-(4′-hydroxy-3′-iso-propylphenoxy)phenol as an off-white solid (0.18 g, 66%): 1H NMR (300 MHz, DMSO-d6): δ 9.95 (s, 1H), 8.91 (s, 1H), 7.27 (s, 2H), 6.62 (d, J=9.0 Hz, 1H), 6.56 (d, J=3.0 Hz, 1H), 6.18 (m, 1H), 3.72 (s, 3H), 3.14 (m, 1H), 1.10 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (7:3); Rf=0.28.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 h
  3. additionThe reaction mixture was poured into ice
  4. extractionextracted with CH2Cl2 (20 mL×2)
  5. dry with materialThe organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel
  9. washeluting with acetone-hexanes (3:7)

Quellen und Nachweise

ORD-Eintrag
ord-721aeda33bc04974ac8cdbd25441fb80
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514419B2

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