反应 #90990

反应方程式

Methyl 3,5-dichloro-4-hydroxybenzoate

bromocyclopentane

potassium carbonate

→

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

收率 84.2%

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

收率 84.2%

溶剂

DMF

反应条件

后处理

1. 1
   其他partitioned between EtOAc (100 mL) and H2O (100 mL)
2. 2
   萃取The aqueous phase was extracted with EtOAc (50 mL)
3. 3
   洗涤the combined organic phases washed successively with water (5×50 mL) and brine (50 mL)
4. 4
   干燥dried over MgSO4
5. 5
   过滤filtered
6. 6
   其他The solvent was removed in vacuo

实验过程

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).

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