Dimethylformamide → 5-Bromo-2-[(2S)-oxiran-2-ylmethoxy]benzaldehyde

HRID 38987

Reaktionsgleichung

Reaktionsgleichung von HRID 38987
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](OS(C1C=CC(C)=CC=1)(=O)=O)[C@H:12]1[O:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C@@H:12]2[CH2:13][O:14]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Produkt 1

HCID 866529415-Bromo-2-[(2S)-oxiran-2-ylmethoxy]benzaldehydeAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Preparation according to Preparation 1 using 5-bromo-2-hydroxybenzaldehyde (6 g, 30 mmol), (S)-glycidyltosylate (8.2 g, 36 mmol), K2CO3 (4.9 g, 36 mmol) and DMF (12 ml). Water (100 ml) was added and the solution was extracted with EtOAc (3×100 ml). The combined organic phases were washed with LiCl (5%, 100 ml), HCl (1 N, 100 ml), brine, were dried and concentrated to give the crude title compound (8.3 g). MS m/z (rel. intensity, 70 eV) 257 (M+, 38), 256 (M+, 39), 200 (bp), 199 (87), 57 (88).

Aufarbeitung

  1. customPreparation
  2. extractionthe solution was extracted with EtOAc (3×100 ml)
  3. washThe combined organic phases were washed with LiCl (5%, 100 ml), HCl (1 N, 100 ml), brine
  4. customwere dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-03d4c742822045a0b1b79b9068c24fe4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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