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6-bromo-2-naphthalenecarboxylic acid

Compound M

6-bromo-2-naphthalenecarboxylic acid

ethanol

sulfuric acid

→

title compound

Ethyl 6-bromo-2-naphthalenecarboxylate

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후처리

1. 1
   온도The solution was refluxed for 30 minutes
2. 2
   기타the reaction mixture partitioned between pentane (100 ml) and water (100 ml)
3. 3
   추출The aqueous phase was extracted with pentane (100 ml)
4. 4
   세척the combined organic layers washed with saturated aqueous NaCl (100 ml)
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated
7. 7
   기타to yield an off-white solid
8. 8
   기타Purification by flash chromatography (silica, 10% EtOAc-hexane)

실험 절차

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 refluxed 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).

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