Synthesis
Under stirring conditions, 1.0 g (2.70 mmol) of dehydrated-8-hydroxymercuric-1-naphthalenecarboxylic acid 26 was added to a mixture of 1.0 mL (67 mmol) acetic acid and 0.40 mL (22.2 mmol) H2O, and the suspension was stirred for 10 min at 0 °C. Subsequently, 0.89 g (8.66 mmol) of NaBr dissolved in 3.2 mL of water and 0.43 g (2.70 mmol) of bromine were added sequentially and the reaction system was slowly heated to 100 °C. After completion of the reaction, it was cooled to room temperature and the mixture was poured into ice and filtered to give 0.57 g (84% yield) of 8-bromo-1-naphthalenecarboxylic acid as a cream-colored solid with a melting point of 173-174 °C (literature value: 174-175 °C). The product was characterized by 1H NMR (500 MHz, DMSO-d6) and 13C NMR (125.77 MHz, DMSO-d6) with the following data: 1H NMR δ 7.49 (t, J = 7.8 Hz, 1H), 7.61 (t, J = 7.3 Hz, 1H), 7.68 (d, J = 7.0 Hz, 1H), 7.96 (d, J = 7.3 Hz, 1H), 8.07 (d, J=8.0 Hz, 1H), 8.11 (d, J=8.0 Hz, 1H), 13.32 (s, 1H); 13C NMR δ119.3,126.3,127.6,128.0,128.3,129.4,131.2,133.6,133.9,135.7, 171.3.
References
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
[2] Journal of Organic Chemistry, 1983, vol. 48, # 17, p. 2926 - 2928
