Benzyl Bromide → 5-(Benzyloxy)-2-bromobenzonitrile

HRID 1850725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850725
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]#[N:10].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH2:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH:4]=1)[C:9]#[N:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 153231112-Bromo-5-hydroxybenzonitrile

Produkt 1

HCID 121019865-(Benzyloxy)-2-bromobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-bromo-3-cyanophenol (1 g, 5.05 mmol) was dissolved in DMF (10 ml) and K2CO3 (1.40 g, 10.10 mmol) and benzyl bromide (0.66 ml, 5.56 mmol) added. The mixture was stirred under N2 for 1 hr at RT. The mixture was diluted with water (15 mL) and extracted with EtOAc (2×10 mL). The organic fractions were combined, washed with brine (saturated, 1×8 mL), dried over MgSO4, filtered and the volatiles removed in vacuo. The residue was purified by chromatography on silica gel Biotage 25M, using a gradient eluant of EtOAc/Hexane (0-50%) to afford the title compound. LC/MS (m/z): 289 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc (2×10 mL)
  2. washwashed with brine (saturated, 1×8 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by chromatography on silica gel Biotage 25M

Quellen und Nachweise

ORD-Eintrag
ord-f4ebb45edb8e4e43989e82cd627d0888
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957062B2

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