Bromine → 2-Bromo-3,5-dimethoxybenzaldehyde

HRID 2061362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061362
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[O:7].[Br:13]Br>C(O)(=O)C>[Br:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:6]=[O:7]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 817473,5-Dimethoxybenzaldehyde

Produkt 1

HCID 114631512-Bromo-3,5-dimethoxybenzaldehydeAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3,5-dimethoxybenzaldehyde (12.6 g, 76 mmol) was dissolved in acetic acid (350 mL). The resulting colourless solution was cooled to 0° C. A solution of bromine (3.9 mL) in acetic acid (50 mL) was added dropwise over 1 h. Once the addition was complete the ice bath was removed and the resulting pale green solution was stirred overnight at room temperature. Cold water was added to the solution. The resulting white solid was collected by vacuum filteration and rinsed with water. The solid was then redissolved in EtOAc and adsorbed on silica gel. The product was purified by flash chromatography, eluting with hexane/EtOAc (4:1) to give 37 (12.5 g, 66%) as a white solid. m/z=344.98 (M+H). 1H NMR (500 MHz, CDCl3): δ: 10.43 (1H, s, CHO), 7.06 (1H, s, ArH), 6.73 (1H, s, ArH), 3.93 (3H, s, CH3O), 3.86 (3H, s, CH3O). 13C NMR (500 MHz, CDCl3): δ: 192.09 (CHO), 159.92 (C-5), 157.02 (C-3), 134.67 (C-1), 109.12 (C-2), 105.83, 103.37 (C-4 & C-6), 56.60 (OMe), 55.82 (OMe).

Aufarbeitung

  1. additionOnce the addition
  2. customwas removed
  3. additionCold water was added to the solution
  4. customThe resulting white solid was collected by vacuum filteration
  5. washrinsed with water
  6. dissolutionThe solid was then redissolved in EtOAc
  7. customThe product was purified by flash chromatography
  8. washeluting with hexane/EtOAc (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7f7e0cd101dc47efb73fb6f9a2ba3a5c
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283340B2

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