反应详情

温度

0 °C

The title compound can be prepared by two procedures designated as procedure A and procedure B below. The starting material of formula II used in each of these procedures is prepared as follows: A sodium hypochlorite solution was prepared by introducing chlorine gas (11.2 g) into a solution of NaOH (15.3 g) in 200 ml of ice water. Solid (6-bromo-2-naphthalenyl)ethanone [9.5 g, 38.1 mmoles, prepared according to the procedure of R. B. Girdler et al., J. Chem. Soc. (C), 518 (1966)] was added to the stirred sodium hypochlorite solution at 0° C. and then the mixture was heated on a steam bath for 1 hr. The precipitate was removed by filtration. Sodium metabisulfite (5 g) was added to the cooled (0° C.) filtrate. The mixture was adjusted to pH 5 with concentrated HCl. The precipitate was collected and dried. The collected precipitate was crystallized from boiling ethanol by the addition of water to afford 5.5 g (two crops) of 6-bromo-2-naphthalenecarboxylic acid; mp 288°-290° C.; NMR (CDCl3) δ 7.68 (2d, J=8 Hz, J2 =2 Hz, 1H), 7.97 (m, 2H), 8.05 (d, J=8 Hz, 1H), 8.25 (d, H), 8.58 (d, 1H), IR (CHCl3), 2800, 1680, 1625, 1567 cm-1 ; UVλmax (EtOH) 333 nm (ε1080), 323 (880), 317 (1020), 286 (9040), 237 (54,350).

1. customis prepared
2. temperaturethe mixture was heated on a steam bath for 1 hr
3. customThe precipitate was removed by filtration
4. additionSodium metabisulfite (5 g) was added to the
5. customThe precipitate was collected
6. customdried
7. customThe collected precipitate was crystallized
8. additionby the addition of water