Reaktion #69680

Reaktionsgleichung

4-methoxybenzylamine

1,2-bis-bromomethyl-4-chloro-5-methoxy-benzene

Na2CO3

→

5-chloro-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-1H-isoindole

Ausbeute 14.8%

Lösungsmittel

acetone

acetone water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated in vacuo
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in ethyl acetate
3. 3
   Extraktionextracted with 2N HCl
4. 4
   Extraktionextracted with ethyl acetate (×2)
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated under vacuum

Vorschrift

A solution of 4-methoxybenzylamine (2.4 g, 17.6 mmol) in acetone (110 ml) was added dropwise to a mixture of 1,2-bis-bromomethyl-4-chloro-5-methoxy-benzene (assumed theoretical, 17.6 mmol) and Na2CO3 (12 g, 114 mmol) in acetone/water (10 ml:12.5 ml) then stirred at room temperature for 2 hours and concentrated in vacuo. The crude material was dissolved in ethyl acetate and extracted with 2N HCl. The aqueous layer was neutralized with sodium carbonate, extracted with ethyl acetate (×2), dried (MgSO4) and evaporated under vacuum to give 5-chloro-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-1H-isoindole (0.8 g, 2.6 mmol) as a brown gum. MS: [M+H]+ 304

Quelle