Cesium carbonate → Tert-butyl 2-(2-bromo-4-formylphenoxy)acetate

HRID 68583

Reaktionsgleichung

Reaktionsgleichung von HRID 68583
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[O:10][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 17999215Tert-butyl 2-(2-bromo-4-formylphenoxy)acetateAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-4-hydroxybenzaldehyde (5 g, 25 mmol, 1 eq, Aldrich, Milwaukee, Wis., USA) in DMF (200 mL) was added solid cesium carbonate (16.25 g, 50 mmol, 2 eq) followed by dropwise addition of t-butyl 2-bromoacetate (4.4 mL, 30 mmol, 1.2 eq, Aldrich, Milwaukee, Wis., USA). After stirring at room temperature for 18 h, the DMF was removed in vacuo and the resultant residue was extracted between EtOAc (50 mL) and brine (50 mL). The separated organic layer was dried (Na2SO4), and concentrated in vacuo to give 7.74 g (98.4%) of t-butyl 2-(2-bromo-4-formylphenoxy)acetate (1). 1HNMR (CDCl3, 300 MHz): δ 9.83 (s, 1H), 8.08 (d, 1H), 7.76 (dd, 1H), 6.83 (d, 1H), 4.67 (s, 1H).1.44 (s, 9H).

Aufarbeitung

  1. customthe DMF was removed in vacuo
  2. extractionthe resultant residue was extracted between EtOAc (50 mL) and brine (50 mL)
  3. dry with materialThe separated organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-03cdefa305c4419ab250d0cc1ffdea8f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822467B2

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