Réaction #66990

Équation de réaction

3-fluoro-4-hydroxybenzaldehyde

K2CO3

2-bromoethyl acetate

→

aldehyde

Rendement 51.0%

4-(2-acetoxy-ethoxy)-3-fluoro-benzaldehyde

Rendement 51.0%

Solvants

acetone

diethyl ether

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (3×50 mL)
2. 2
   ExtractionThe organic extract
3. 3
   Séchageis dried over MgSO4
4. 4
   AutreThe remaining residue is chromatographed on silica gel

Mode opératoire

A mixture of 3-fluoro-4-hydroxybenzaldehyde (2.0 g, 14.3 mmol), K2CO3 (5.92 g, 42.8 mmol) and 2-bromoethyl acetate (4.77 g, 28.5 mmol) in acetone (30 mL) is stirred at 55° C. for 24 h before it is diluted with diethyl ether (150 mL) and washed with water (3×50 mL). The organic extract is dried over MgSO4 and concetrated. The remaining residue is chromatographed on silica gel to give the title aldehyde (1.65 g) as a colourless oil. 1H NMR (CDCl3): δ 9.85 (s, 1H), 7.64-7.58 (m, 2H), 7.07 (t, J=8.2 Hz, 1H), 4.49-4.45 (m, 2H), 4.35-4.30 (m, 2H), 2.10 (s, 3H).

Source