Reaktion #364482

Reaktionsgleichung

water

3-Bromobenzaldehyde

N-acetyl glycine

sodium acetate

→

methyl m-bromo-α-acetamidocinnamate

Lösungsmittel

MeOH

acetic anhydride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 1 h
2. 2
   FiltrationThe resulting suspension was filtered
3. 3
   Waschenthe solid was washed with water (2×50 mL)
4. 4
   workup.DISSOLUTIONThe remaining solid was dissolved in methylene chloride (100 mL)
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeto give a yellow solid
9. 9
   Temperaturheated
10. 10
    Temperaturto reflux for 9 h
11. 11
    EinengenThe reaction mixture was concentrated in vacuo
12. 12
    Sonstigeto give a yellow solid
13. 13
    SonstigeRecrystallization from EtOAc and petroleum ether

Vorschrift

3-Bromobenzaldehyde (23.7 g, 128.2 mmol), N-acetyl glycine (10.0 g, 85.5 mmol) and sodium acetate (5.26 g, 64.1 mmol) in acetic anhydride (60 mL) was heated to reflux for 1 h. The reaction was cooled to room temperature and water (100 mL) was added. The resulting suspension was filtered and the solid was washed with water (2×50 mL). The remaining solid was dissolved in methylene chloride (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. The solid was suspended in dry MeOH (200 mL) and heated to reflux for 9 h. The reaction mixture was concentrated in vacuo to give a yellow solid. Recrystallization from EtOAc and petroleum ether gave methyl m-bromo-α-acetamidocinnamate as a yellow solid. MS (CI) m/z 298 (M++1 (Br=79), 100%), 300 (M++1 (Br=81), 100%). 13C NMR (50 MHz, d6-DMSO): δ23.3, 52.8, 122.5, 125.0, 128.06, 130.0, 130.2, 132.2, 132.3, 135.9, 165.4 and 168.8.

Quelle