Triphenylphosphine → 5-(Bromomethyl)-2-furaldehyde

HRID 336835

Reaktionsgleichung

Reaktionsgleichung von HRID 336835
[OH:1][CH2:2][C:3]1[O:7][C:6]([CH:8]=O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>ClCCl>[Br:29][CH2:8][C:6]1[O:7][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2373325-(Hydroxymethyl)furfural

Produkt 1

HCID 119704915-(Bromomethyl)-2-furaldehydeAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of 3.4 g (26.7 mmol) of 5-(hydroxymethyl)furan-2-carboxaldehyde and 7.78 g (29.4 mmol) of triphenylphosphine in 300 ml of dichloromethane at −5° C. are added 5.28 g (29.4 mmol) of N-bromosuccinimide in 10 min. The mixture is stirred at −5° C. for 30 min. The mixture is then concentrated and the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3) to yield 4.38 g (87%) of 5-(bromomethyl)furan-2-carboxaldehyde in the form of a brown solid.

Aufarbeitung

  1. concentrationThe mixture is then concentrated
  2. customthe residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-3384ac6afaf846c187cbe481e7a64ad1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889711B2

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