Reaktion #90990

Reaktionsgleichung

Methyl 3,5-dichloro-4-hydroxybenzoate

bromocyclopentane

potassium carbonate

→

methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate

Ausbeute 84.2%

Methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate

Ausbeute 84.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between EtOAc (100 mL) and H2O (100 mL)
2. 2
   ExtraktionThe aqueous phase was extracted with EtOAc (50 mL)
3. 3
   Waschenthe combined organic phases washed successively with water (5×50 mL) and brine (50 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   SonstigeThe solvent was removed in vacuo

Vorschrift

Methyl 3,5-dichloro-4-hydroxybenzoate (1) (1.00 g, 4.52 mmol) was dissolved in DMF (8 mL) and treated with bromocyclopentane (534 μL, 4.98 mmol), followed by potassium carbonate (937 mg, 6.79 mmol). The mixture was stirred at 80° C. for 3 h and then partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous phase was extracted with EtOAc (50 mL) and the combined organic phases washed successively with water (5×50 mL) and brine (50 mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo to afford methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate (2) (1.10 g, 84%): 1H NMR (400 MHz, CDCl3) δ: 7.97 (2H, s), 5.04 (1H, m), 3.90 (3H, s), 2.04-1.91 (4H, m), 1.82-1.75 (2H, m), 1.69-1.60 (2H, m).

Quelle