反应 #411407

反应方程式

6-bromo-2-naphthalenecarboxylic acid

Compound M

6-bromo-2-naphthalenecarboxylic acid

ethanol

sulfuric acid

→

title compound

Ethyl 6-bromo-2-naphthalenecarboxylate

反应条件

后处理

1. 1
   其他for 30 minutes
2. 2
   其他the reaction mixture partitioned between pentane (100 ml) and water (100 ml)
3. 3
   萃取The aqueous phase was extracted with pentane (100 ml)
4. 4
   洗涤the combined organic layers washed with saturated aqueous NaCl (100 ml), dried MgSO4), and
5. 5
   浓缩concentrated
6. 6
   其他to yield an off-white solid
7. 7
   其他Purification by flash chromatography (silica, 10% EtOAc-hexane)

实验过程

To a solution of 6-bromo-2-naphthalenecarboxylic acid (Compound M) 3.1 g, (12.43 mmol) in ethanol (30 ml, 23.55 g, 511.0 mmol) was added 18M sulfuric acid (2 ml). The solution was Tefluxed for 30 minutes, cooled to room temperature, and the reaction mixture partitioned between pentane (100 ml) and water (100 ml). The aqueous phase was extracted with pentane (100 ml) and the combined organic layers washed with saturated aqueous NaCl (100 ml), dried MgSO4), and concentrated to yield an off-white solid. Purification by flash chromatography (silica, 10% EtOAc-hexane) afforded the title compound as a white solid. 1H NMR (CDCl3): δ 8.58 (1H, br s), 8.10 (1H, dd, J=1.7, 9 Hz), 8.06 (1H, d, J=2 Hz), 7.83 (1H, d, J=9 Hz), 7.80 (1H, d, J=9 Hz), 7.62 (1H, dd, J=2, 9 Hz).

来源