반응 #90990

반응 방정식

Methyl 3,5-dichloro-4-hydroxybenzoate

bromocyclopentane

potassium carbonate

→

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

수율 84.2%

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

수율 84.2%

용매

DMF

반응 조건

후처리

1. 1
   기타partitioned between EtOAc (100 mL) and H2O (100 mL)
2. 2
   추출The aqueous phase was extracted with EtOAc (50 mL)
3. 3
   세척the combined organic phases washed successively with water (5×50 mL) and brine (50 mL)
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   기타The solvent was removed in vacuo

실험 절차

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).

출처