Boron tribromide → 2-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile

HRID 636715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636715
[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23]C)[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[OH:23])[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 155236442-(3-Isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile

Produkt 1

HCID 155236452-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrileAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a cooled (−78° C.), stirred solution of 2-(3-isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile (308 mg) in dichloromethane (5 mL) was added boron tribromide (0.31 mL) dropwise. The reaction was allowed to warm to RT and stirred for 1 h, quenched with water and stirred for 20 min. The reaction was extracted with ethyl acetate, the organic phase washed with water, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo. Flash chromatography (20% ethyl acetate/hexanes) on silica gel afforded 2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile as a yellow oil (215 mg).

Aufarbeitung

  1. temperatureto warm to RT
  2. customquenched with water
  3. stirringstirred for 20 min
  4. extractionThe reaction was extracted with ethyl acetate
  5. washthe organic phase washed with water, saturated aqueous brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-120220b3c7d54ca9be48964a1e182d0a
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194454B1

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