Carbon tetrabromide → 4-(Bromomethyl)-2-hydroxybenzonitrile

HRID 379024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379024
[OH:1][C:2]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>CN(C=O)C.C(Cl)Cl>[Br:32][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([OH:1])[CH:9]=1

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 216969742-Hydroxy-4-(hydroxymethyl)benzonitrile

Produkt 1

HCID 216969934-(Bromomethyl)-2-hydroxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Hydroxy-4-hydroxymethylbenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL)—CH2Cl2(5 mL) and treated with triphenylphosphine (0.53 g, 2.01 mmol) and carbon tetrabromide (0.67 g, 2.01 mmol) at ambient temperature with stirring. After 2 h the reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL), the organic layer separated, dried (MgSO4), and filtered to give the title compound after silica gel chromatography (15% EtOAc/hexane to 25% EtOAc/hexane).

Aufarbeitung

  1. customAfter 2 h the reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL)
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8991a41115b445c2baca422ec49769a8
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297239B1

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