Boron tribromide → 7-Hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 20047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20047
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:15])([CH3:14])[CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:15])([CH3:14])[CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 12226463HCID 12226463, Verbindung

Produkt 1

HCID 673052057-Hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

7-Methoxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one (2.25 g, 11.0 mmol)was dissolved in 30 ml CH2Cl2 and cooled to −78° C. Boron tribromide (25.000 ml, 25.0 mmol) was added and the reaction was stirred for 6 h. The temperature was elevated to 0° C. during this time. The mixture was pored into ice and extracted 3×EtOAc (300 ml each). The combined organic extracts were dried over MgSO4 and evaporated. Glass col. Chrom. gave 7-hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one as a yellow solid. MS m/z: 191.1 (M+1).

Aufarbeitung

  1. customwas elevated to 0° C. during this time
  2. extractionextracted 3×EtOAc (300 ml each)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-806341c4d81241c9a119bf0f1e730f90
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745484B2

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